Hiroto Yoshida

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Organization: Hiroshima University

Department: Department of Applied Chemistry

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Chemicals
References

B(MIDA)-Containing Diborons

Co-reporter:Hiroto Yoshida, Michinari Seki, Ikuo Kageyuki, Itaru Osaka, Sayaka Hatano, and Manabu Abe

ACS Omega September 2017? Volume 2(Issue 9) pp:5911-5911

Publication Date(Web):September 18, 2017

DOI:10.1021/acsomega.7b01042

Unsymmetrical B(MIDA)-containing diborons of potential synthetic utility were found to be synthesized from the readily available (neop)B–B(neop) and (HO)2B–B(OH)2, and the procedure was extended to the generation of symmetrical (MIDA)B–B(MIDA). NMR and X-ray crystal structure studies revealed that B(MIDA) units of all of the diborons obtained in this study were in rigid tetrahedral environment.Topics: Crystal structure; Group 13 compounds; Group 13 compounds; Molecular structure;

Copper-Catalyzed Borylstannylation of Alkynes with Tin Fluorides

Co-reporter:Hiroto Yoshida, Miki Kimura, Itaru Osaka, and Ken Takaki

Organometallics April 10, 2017 Volume 36(Issue 7) pp:1345-1345

Publication Date(Web):March 24, 2017

DOI:10.1021/acs.organomet.7b00058

Tin fluorides were found to be suitable electrophiles for the copper-catalyzed borylstannylation of terminal alkynes with bis(pinacolato)diboron to afford cis-vic-boryl(stannyl)alkenes straightforwardly. A fluorine atom proved to play a pivotal role in generating a key catalytic intermediate, a borylcopper species, both in the induction period and in the σ-bond metathesis step.

Copper-catalyzed direct borylation of alkyl, alkenyl and aryl halides with B(dan)

Co-reporter:Hiroto Yoshida;Yuki Takemoto;Shintaro Kamio;Itaru Osaka;Ken Takaki

Organic Chemistry Frontiers 2017 vol. 4(Issue 7) pp:1215-1219

Publication Date(Web):2017/06/27

DOI:10.1039/C7QO00084G

Substitutional borylation of C(sp3 or sp2)–halogen bonds with an unsymmetrical diboron [(pin)B–B(dan)] was found to proceed smoothly under copper catalysis. A variety of masked alkyl-, alkenyl- and arylboron compounds [R–B(dan)] were straightforwardly accessible with high functional group compatibility in high yield.

Copper-Catalyzed B(dan)-Installing Carboboration of Alkenes

Co-reporter:Ikuo Kageyuki, Itaru Osaka, Ken Takaki, and Hiroto Yoshida

Organic Letters 2017 Volume 19(Issue 4) pp:

Publication Date(Web):February 3, 2017

DOI:10.1021/acs.orglett.6b03820

Carboboration of alkenes was found to occur readily with an unsymmetrical diboron [(pin)B–B(dan)] and alkyl halides under copper catalysis, leading to the direct formation of protected alkylboron compounds via synchronous C–C and C–B bond-forming processes. The B(dan) moiety was solely installed into the organic frameworks with the regioselective attachment to a terminal carbon of alkenes employed.

Inside Cover: Aryne–Imine–Aryne Coupling Reaction via [4+2] Cycloaddition between Aza-o-Quinone Methides and Arynes (Asian J. Org. Chem. 8/2017)

Co-reporter: Dr. Hiroto Yoshida;Hitoshi Kuriki;Shori Fujii;Yu Ito; Dr. Itaru Osaka; Dr. Ken Takaki

Asian Journal of Organic Chemistry 2017 Volume 6(Issue 8) pp:944-944

Publication Date(Web):2017/08/01

DOI:10.1002/ajoc.201700298

Aryne–imine–aryne coupling: Two molar amounts of arynes have been formally inserted into carbon−nitrogen double bonds of imines. This aryne–imine–aryne coupling reaction selectively produces acridane derivatives via intermediary generation of transient aza-o-quinone methides. The use of imines with steric bulk at the imine carbon, which leads to preferential formation of ‘outward’ aza-o-quinone methides, is the key for this reaction. More information can be found in the Communication by Hiroto Yoshida et al. on page 973 in Issue 8, 2017 (DOI: 10.1002/ajoc.201700251).

Aryne–Imine–Aryne Coupling Reaction via [4+2] Cycloaddition between Aza-o-Quinone Methides and Arynes

Co-reporter: Dr. Hiroto Yoshida;Hitoshi Kuriki;Shori Fujii;Yu Ito; Dr. Itaru Osaka; Dr. Ken Takaki

Asian Journal of Organic Chemistry 2017 Volume 6(Issue 8) pp:973-976

Publication Date(Web):2017/08/01

DOI:10.1002/ajoc.201700251

AbstractA direct method for the synthesis of acridane derivatives based upon a 2:1 coupling reaction between arynes and imines was developed. The reaction proceeds through formation of transient aza-ortho-quinone methides arising from a net [2+2] cycloaddition between arynes and imines. Introduction of steric bulk into an imine carbon has proven to be vital for this facile coupling.

Borylation of Alkynes under Base/Coinage Metal Catalysis: Some Recent Developments

Co-reporter:Hiroto Yoshida

ACS Catalysis 2016 Volume 6(Issue 3) pp:1799

Publication Date(Web):February 3, 2016

DOI:10.1021/acscatal.5b02973

Alkenylboranes have been vital reagents in modern synthetic organic chemistry, whose carbon–boron bond is transformable into a carbon–carbon bond stereoretentively to give such invaluable mutisubstituted alkenes as natural products, biologically active molecules, and functional materials. Introduction of a boryl moiety across a carbon–carbon triple bond of alkynes (borylation of alkynes) is one of the most direct and potent methods for synthesizing alkenylboranes, and this field has thus far experienced remarkable progress mainly with group 10 transition metal catalysts (Ni, Pd, Pt), which enables highly functionalized alkenylboranes to be constructed stereoselectively. On the other hand, much attention has recently been focused on the appealing catalysis of base (Fe, Co) and coinage (Cu, Ag, Au) metals toward the borylation of alkynes, which is summarized in this perspective.Keywords: alkenylborane synthesis; alkynes; base metal catalysis; boron; coinage metal catalysis; regioselectivity; stereoselectivity

Borylstannylation of alkynes with inverse regioselectivity: copper-catalyzed three-component coupling using a masked diboron

Co-reporter:H. Yoshida, Y. Takemoto and K. Takaki

Chemical Communications 2015 vol. 51(Issue 29) pp:6297-6300

Publication Date(Web):03 Feb 2015

DOI:10.1039/C5CC00439J

A variety of terminal alkynes are facilely convertible into cis-boryl(stannyl)alkenes with inverse regioselectivity to those of the previous borylstannylation by the copper-catalyzed three-component reaction using a masked diboron. The synthetic utility of the resulting boryl(stannyl)alkenes has been demonstrated by chemoselective coupling reactions.

Copper-catalyzed α-selective hydrostannylation of alkynes for the synthesis of branched alkenylstannanes

Co-reporter:H. Yoshida, A. Shinke, Y. Kawano and K. Takaki

Chemical Communications 2015 vol. 51(Issue 53) pp:10616-10619

Publication Date(Web):27 Apr 2015

DOI:10.1039/C5CC02720A

A variety of branched alkenylstannanes can directly be synthesized with excellent α-selectivity by the copper-catalyzed hydrostannylation using a distannane or a silylstannane, irrespective of the electronic and steric characteristics of terminal alkynes employed. Synthetic utility of the resulting branched alkenylstannane has been demonstrated by the total synthesis of bexarotene.

Inverse regioselectivity in the silylstannylation of alkynes and allenes: copper-catalyzed three-component coupling with a silylborane and a tin alkoxide

Co-reporter:H. Yoshida, Y. Hayashi, Y. Ito and K. Takaki

Chemical Communications 2015 vol. 51(Issue 46) pp:9440-9442

Publication Date(Web):14 Apr 2015

DOI:10.1039/C5CC01856K

Silylstannylation of alkynes and allenes has been found to proceed by three-component coupling using a silylborane and a tin alkoxide in the presence of a Cu(I) catalyst. The regioselectivities are completely inverse to those of the conventional silylstannylation under palladium catalysis.

A masked diboron in Cu-catalysed borylation reaction: highly regioselective formal hydroboration of alkynes for synthesis of branched alkenylborons

Co-reporter:Hiroto Yoshida, Yuki Takemoto and Ken Takaki

Chemical Communications 2014 vol. 50(Issue 61) pp:8299-8302

Publication Date(Web):08 Apr 2014

DOI:10.1039/C4CC01757A

The use of a masked diboron as a boron source in the presence of a Cu–N-heterocyclic carbene (NHC) catalyst enables alkyl-, aryl-, heteroatom- and silyl-substituted terminal alkynes to undergo α-selective formal hydroboration to give diverse branched alkenylboron compounds exclusively. Synthetic potential of this α-selective hydroboration has been demonstrated by total synthesis of pharmaceutically significant bexarotene and LG100268.

Silver-Catalyzed Highly Regioselective Formal Hydroboration of Alkynes

Co-reporter:Hiroto Yoshida, Ikuo Kageyuki, and Ken Takaki

Organic Letters 2014 Volume 16(Issue 13) pp:3512-3515

Publication Date(Web):June 13, 2014

DOI:10.1021/ol501465x

A silver(I)–N-heterocyclic carbene complex has proven to be a potent catalyst for formal hydroboration of alkynes, providing a variety of borylalkenes in regio- and stereoselective manners. Under the silver catalysis, allenes also undergo regioselective hydroboration to give borylalkenes.

Direct Synthesis of Boron-Protected Alkenyl- and Alkylborons via Copper-Catalyzed Formal Hydroboration of Alkynes and Alkenes

Co-reporter:Dr. Hiroto Yoshida;Yuki Takemoto;Dr. Ken Takaki

Asian Journal of Organic Chemistry 2014 Volume 3( Issue 11) pp:1204-1209

Publication Date(Web):

DOI:10.1002/ajoc.201402166

Abstract

Formal hydroboration of internal alkynes proceeds regio- and stereoselectively by the use of a diboron reagent masked with 1,8-diaminonaphthalene (dan) in the presence of readily available [(Ph₃P)₃CuCl], leading to direct formation of diverse B-protected alkenylborons in high yield. The B(dan) moiety can also be efficiently installed into the CC double bond of alkenes to afford the respective alkylborons.

Copper-catalyzed distannylation of alkynes

Co-reporter:Hiroto Yoshida, Ayako Shinke and Ken Takaki

Chemical Communications 2013 vol. 49(Issue 99) pp:11671-11673

Publication Date(Web):22 Oct 2013

DOI:10.1039/C3CC47173J

A copper(I)–phosphine complex has been found to facilely promote the distannylation of alkynes with the aid of a base, where a catalytically generated Cu–Sn species serves as a key intermediate. The broad versatility of the copper catalysis has been demonstrated by the facile distannylation of unfunctionalized aliphatic alkynes, being hardly achievable with the conventional palladium catalysts.

Copper-Catalyzed Three-Component Carboboration of Alkynes and Alkenes

Co-reporter:Hiroto Yoshida, Ikuo Kageyuki, and Ken Takaki

Organic Letters 2013 Volume 15(Issue 4) pp:952-955

Publication Date(Web):February 5, 2013

DOI:10.1021/ol4001526

Carboboration of alkynes was found to take place efficiently by a three-component coupling reaction with diboron and carbon electrophiles under copper catalysis to afford diverse multisubstituted borylalkenes in a stereoselective manner. The carboboration was also applicable to alkenes, leading to the formation of multisubstituted borylalkanes via regioselective carbon–boron and carbon–carbon bond-forming processes.

Synchronous ArF and ArSn Bond Formation through Fluorostannylation of Arynes

Co-reporter:Dr. Hiroto Yoshida;Ryuma Yoshida ;Dr. Ken Takaki

Angewandte Chemie International Edition 2013 Volume 52( Issue 33) pp:8629-8632

Publication Date(Web):

DOI:10.1002/anie.201302783

Synchronous ArF and ArSn Bond Formation through Fluorostannylation of Arynes

Co-reporter:Dr. Hiroto Yoshida;Ryuma Yoshida ;Dr. Ken Takaki

Angewandte Chemie 2013 Volume 125( Issue 33) pp:8791-8794

Publication Date(Web):

DOI:10.1002/ange.201302783

Copper-Catalyzed Borylation Reactions of Alkynes and Arynes

Co-reporter: Hiroto Yoshida;Shota Kawashima;Yuki Takemoto;Kengo Okada; Joji Ohshita ; Ken Takaki

Angewandte Chemie 2012 Volume 124( Issue 1) pp:239-242

Publication Date(Web):

DOI:10.1002/ange.201106706

Copper-Catalyzed Three-Component Borylstannylation of Alkynes

Co-reporter:Yuki Takemoto;Dr. Hiroto Yoshida;Dr. Ken Takaki

Chemistry - A European Journal 2012 Volume 18( Issue 46) pp:14841-14844

Publication Date(Web):

DOI:10.1002/chem.201202435

Abstract

Regio- and stereoselective installation of boryl and stannyl moieties into a carbon–carbon triple bond of various alkynes has been achieved based on a three-component coupling reaction by using a diboron and a tin alkoxide with the aid of a copper(II) acetate–tricyclohexylphosphine complex, giving diverse vic-borylstannylalkenes in a straightforward manner. Carbon–tin and carbon–boron bonds of the resulting borylstannylation product are successively transformed into carbon–carbon bonds by a Migita–Kosugi–Stille and a Suzuki–Miyaura coupling, leading to the formation of (Z)-tamoxifen with anti-breast cancer activity.

Copper-Catalyzed Borylation Reactions of Alkynes and Arynes

Co-reporter: Hiroto Yoshida;Shota Kawashima;Yuki Takemoto;Kengo Okada; Joji Ohshita ; Ken Takaki

Angewandte Chemie International Edition 2012 Volume 51( Issue 1) pp:235-238

Publication Date(Web):

DOI:10.1002/anie.201106706

Three-component coupling using arynes and DMF: straightforward access to coumarinsvia ortho-quinone methides

Co-reporter:Hiroto Yoshida, Yu Ito and Joji Ohshita

Chemical Communications 2011 vol. 47(Issue 30) pp:8512-8514

Publication Date(Web):24 May 2011

DOI:10.1039/C1CC11955A

ortho-Quinone methides, arising from a formal [2+2] cycloaddition between arynes and DMF, were found to facilely undergo a [4+2] cycloaddition with ester enolates or ketenimine anions to produce diverse coumarins in a straightforward manner.

Aryne reaction with trifluoromethyl ketones in three modes: C–C bond cleavage, [2+2] cycloaddition and O-arylation

Co-reporter:Hiroto Yoshida, Yu Ito, Yunito Yoshikawa, Joji Ohshita and Ken Takaki

Chemical Communications 2011 vol. 47(Issue 30) pp:8664-8666

Publication Date(Web):27 Jun 2011

DOI:10.1039/C1CC12820E

Trifluoromethyl ketones were found to be coupled with arynes in three modes depending upon their substitution patterns, namely C–C bond cleavage, [2+2] cycloaddition and O-arylation.

Three-Component Coupling of Arynes and Organic Bromides

Co-reporter: Hiroto Yoshida;Yuji Asatsu;Yasuhiro Mimura;Yu Ito; Joji Ohshita ; Ken Takaki

Angewandte Chemie International Edition 2011 Volume 50( Issue 41) pp:9676-9679

Publication Date(Web):

DOI:10.1002/anie.201104858

Three-Component Coupling of Arynes and Organic Bromides

Co-reporter: Hiroto Yoshida;Yuji Asatsu;Yasuhiro Mimura;Yu Ito; Joji Ohshita ; Ken Takaki

Angewandte Chemie 2011 Volume 123( Issue 41) pp:9850-9853

Publication Date(Web):

DOI:10.1002/ange.201104858

Facile access to boryltetralins and borylnaphthalenes via a cycloaddition using o-quinodimethanes

Co-reporter:Hiroto Yoshida, Masashi Mukae and Joji Ohshita

Chemical Communications 2010 vol. 46(Issue 29) pp:5253-5255

Publication Date(Web):25 Jun 2010

DOI:10.1039/C002949A

Borylalkenes are found to serve as efficient dienophiles in a cycloaddition reaction with o-quinodimethanes, giving diverse boryltetralins, which are convertible into borylnaphthalenes via an oxidative aromatization.

Platinum-catalysed diborylation of arynes: synthesis and reaction of 1,2-diborylarenes

Co-reporter:Hiroto Yoshida, Kengo Okada, Shota Kawashima, Kenji Tanino and Joji Ohshita

Chemical Communications 2010 vol. 46(Issue 10) pp:1763-1765

Publication Date(Web):13 Jan 2010

DOI:10.1039/B919407J

Arynes are found to be facilely inserted into bis(pinacolato)diboron by using a platinum–isocyanide catalyst, affording diverse 1,2-diborylarenes, which can be converted into o-terphenyls via Suzuki–Miyaura coupling reaction.

Copper-catalysed bromoalkynylation of arynes

Co-reporter:Takami Morishita, Hiroto Yoshida and Joji Ohshita

Chemical Communications 2010 vol. 46(Issue 4) pp:640-642

Publication Date(Web):18 Nov 2009

DOI:10.1039/B919301D

Arynes were found to be inserted into a C(sp)–Br σ-bond of bromoalkynes in the presence of a copper catalyst, giving (alkynyl)bromoarenes in a straightforward manner.

Fluorenes as new molecular scaffolds for carbon–carbon σ-bond cleavage reaction: acylfluorenylation of arynes

Co-reporter:Hiroto Yoshida, Takeshi Kishida, Masahiko Watanabe and Joji Ohshita

Chemical Communications 2008 (Issue 45) pp:5963-5965

Publication Date(Web):08 Oct 2008

DOI:10.1039/B814597K

Acyl and fluorenyl moieties are facilely installed into neighbouring positions of aromatic skeletons via C–C bond cleavage reaction using arynes.

Insertion of arynes into carbon–halogen σ-bonds: regioselective acylation of aromatic rings

Co-reporter:Hiroto Yoshida, Yasuhiro Mimura, Joji Ohshita and Atsutaka Kunai

Chemical Communications 2007 (Issue 23) pp:2405-2407

Publication Date(Web):09 Mar 2007

DOI:10.1039/B701581J

Arynes were found to insert into carbon–halogen σ-bonds of various acid halides, enabling acyl and halogen moieties to be introduced simultaneously into adjacent positions of aromatic rings.

Straightforward construction of diarylmethane skeletons via aryne insertion into carbon–carbon σ-bonds

Co-reporter:Hiroto Yoshida, Masahiko Watanabe, Takami Morishita, Joji Ohshita and Atsutaka Kunai

Chemical Communications 2007 (Issue 15) pp:1505-1507

Publication Date(Web):05 Feb 2007

DOI:10.1039/B616768C

Two molar amounts of arynes were found to couple with nitriles via carbon–carbon σ-bond cleavage, assembling diverse diarylmethane skeletons in a straightforward manner.

Palladium-catalysed dimerisation–distannylation of arynes: synthesis and reaction of 2,2′-distannylbiaryls

Co-reporter:Hiroto Yoshida, Kenji Tanino, Joji Ohshita and Atsutaka Kunai

Chemical Communications 2005 (Issue 45) pp:5678-5680

Publication Date(Web):18 Oct 2005

DOI:10.1039/B511773A

Two molar amounts of arynes were found to insert into a Sn–Sn bond of a distannane in the presence of a sub-stoichiometric amount of a palladium-phosphite complex, affording straightforwardly 2,2′-distannylbiaryls.

Facile insertion reaction of arynes into carbon–carbon σ-bonds

Co-reporter:Hiroto Yoshida, Masahiko Watanabe, Joji Ohshita and Atsutaka Kunai

Chemical Communications 2005 (Issue 26) pp:3292-3294

Publication Date(Web):01 Jun 2005

DOI:10.1039/B505392G

The carbon–carbon σ-bond of various β-dicarbonyl compounds was found to add to the triple bond of arynes under extremely mild conditions, leading to direct introduction of different carbon functional groups into the aromatic skeletons.

Thiostannylation of arynes with stannyl sulfides: synthesis and reaction of 2-(arylthio)arylstannanes

Co-reporter:Hiroto Yoshida, Tsuguaki Terayama, Joji Ohshita and Atsutaka Kunai

Chemical Communications 2004 (Issue 17) pp:1980-1981

Publication Date(Web):08 Jul 2004

DOI:10.1039/B405883F

Arynes were found to insert into a sulfur–tin σ-bond of stannyl sulfides to give a variety of 2-(arylthio)arylstannanes, whose carbon–tin bonds were applicable to further transformations.

Distannylation of Strained Carbon–Carbon Triple Bonds Catalyzed by a Palladium Complex

Co-reporter:Hiroto Yoshida Dr.;Kenji Tanino;Joji Ohshita ;Atsutaka Kunai

Angewandte Chemie 2004 Volume 116(Issue 38) pp:

Publication Date(Web):22 SEP 2004

DOI:10.1002/ange.200460189

Die oxidative Addition eines Distannans an einen Palladium(0)-Komplex ist der entscheidende Schritt bei der Distannylierung von in situ erzeugten Arinen mit Distannanen in Gegenwart einer katalytischen Menge eines Palladium/tert-Octylisocyanid(tOcNC)-Komplexes. Gebildet werden 1,2-Distannylarene in mäßigen bis hohen Ausbeuten (siehe Schema). Auch Bisarine und Cyclohexine können als Substrate verwendet werden.

Arynes in a Three-Component Coupling Reaction: Straightforward Synthesis of Benzoannulated Iminofurans

Co-reporter:Hiroto Yoshida Dr.;Hiroyuki Fukushima;Joji Ohshita ;Atsutaka Kunai

Angewandte Chemie 2004 Volume 116(Issue 30) pp:

Publication Date(Web):20 JUL 2004

DOI:10.1002/ange.200460009

Misch die Komponenten, rühr um und … voilà! Eine Vielzahl benzoanellierter Iminofurane kann auf diese einfache Art aus einem Arin, einem Isocyanid und einem Aldehyd in akzeptablen bis guten Ausbeuten erhalten werden (siehe Schema). Mit einem 3-substituierten Arin und mit 4-Fluorbenzin war die Regioselektivität perfekt, während 4-Methylbenzin ein Gemisch aus Regioisomeren lieferte.

Distannylation of Strained Carbon–Carbon Triple Bonds Catalyzed by a Palladium Complex

Co-reporter:Hiroto Yoshida Dr.;Kenji Tanino;Joji Ohshita ;Atsutaka Kunai

Angewandte Chemie International Edition 2004 Volume 43(Issue 38) pp:

Publication Date(Web):22 SEP 2004

DOI:10.1002/anie.200460189

Oxidative addition of a distannane to a palladium(0) complex occurs during the distannylation of in situ generated arynes with distannanes in the presence of a catalytic amount of a palladium/tert-octyl isocyanide (tOcNC) complex to give 1,2-distannylarenes in moderate to high yields (see scheme). Bisarynes and cyclohexynes can also be used as substrates for the reaction.

Arynes in a Three-Component Coupling Reaction: Straightforward Synthesis of Benzoannulated Iminofurans

Co-reporter:Hiroto Yoshida Dr.;Hiroyuki Fukushima;Joji Ohshita ;Atsutaka Kunai

Angewandte Chemie International Edition 2004 Volume 43(Issue 30) pp:

Publication Date(Web):20 JUL 2004

DOI:10.1002/anie.200460009

Mix the components, stir, and … voilà! A variety of benzoannulated iminofurans can be obtained in this straightforward manner from an aryne, an isocyanide, and an aldehyde in modest to high yields (see scheme). Perfect regioselectivity was observed with a 3-substituted aryne and 4-fluorobenzyne, whereas 4-methylbenzyne gave a mixture of regioisomers.

Borylstannylation of alkynes with inverse regioselectivity: copper-catalyzed three-component coupling using a masked diboron

Co-reporter:H. Yoshida, Y. Takemoto and K. Takaki

Chemical Communications 2015 - vol. 51(Issue 29) pp:NaN6300-6300

Publication Date(Web):2015/02/03

DOI:10.1039/C5CC00439J

Copper-catalyzed direct borylation of alkyl, alkenyl and aryl halides with B(dan)

Co-reporter:Hiroto Yoshida, Yuki Takemoto, Shintaro Kamio, Itaru Osaka and Ken Takaki

Inorganic Chemistry Frontiers 2017 - vol. 4(Issue 7) pp:

Publication Date(Web):

DOI:10.1039/C7QO00084G

Copper-catalyzed α-selective hydrostannylation of alkynes for the synthesis of branched alkenylstannanes

Co-reporter:H. Yoshida, A. Shinke, Y. Kawano and K. Takaki

Chemical Communications 2015 - vol. 51(Issue 53) pp:NaN10619-10619

Publication Date(Web):2015/04/27

DOI:10.1039/C5CC02720A

A masked diboron in Cu-catalysed borylation reaction: highly regioselective formal hydroboration of alkynes for synthesis of branched alkenylborons

Co-reporter:Hiroto Yoshida, Yuki Takemoto and Ken Takaki

Chemical Communications 2014 - vol. 50(Issue 61) pp:NaN8302-8302

Publication Date(Web):2014/04/08

DOI:10.1039/C4CC01757A

Copper-catalyzed distannylation of alkynes

Co-reporter:Hiroto Yoshida, Ayako Shinke and Ken Takaki

Chemical Communications 2013 - vol. 49(Issue 99) pp:NaN11673-11673

Publication Date(Web):2013/10/22

DOI:10.1039/C3CC47173J

Three-component coupling using arynes and DMF: straightforward access to coumarinsvia ortho-quinone methides

Co-reporter:Hiroto Yoshida, Yu Ito and Joji Ohshita

Chemical Communications 2011 - vol. 47(Issue 30) pp:NaN8514-8514

Publication Date(Web):2011/05/24

DOI:10.1039/C1CC11955A

Platinum-catalysed diborylation of arynes: synthesis and reaction of 1,2-diborylarenes

Co-reporter:Hiroto Yoshida, Kengo Okada, Shota Kawashima, Kenji Tanino and Joji Ohshita

Chemical Communications 2010 - vol. 46(Issue 10) pp:NaN1765-1765

Publication Date(Web):2010/01/13

DOI:10.1039/B919407J

Facile access to boryltetralins and borylnaphthalenes via a cycloaddition using o-quinodimethanes

Co-reporter:Hiroto Yoshida, Masashi Mukae and Joji Ohshita

Chemical Communications 2010 - vol. 46(Issue 29) pp:NaN5255-5255

Publication Date(Web):2010/06/25

DOI:10.1039/C002949A

Aryne reaction with trifluoromethyl ketones in three modes: C–C bond cleavage, [2+2] cycloaddition and O-arylation

Co-reporter:Hiroto Yoshida, Yu Ito, Yunito Yoshikawa, Joji Ohshita and Ken Takaki

Chemical Communications 2011 - vol. 47(Issue 30) pp:NaN8666-8666

Publication Date(Web):2011/06/27

DOI:10.1039/C1CC12820E

Trifluoromethyl ketones were found to be coupled with arynes in three modes depending upon their substitution patterns, namely C–C bond cleavage, [2+2] cycloaddition and O-arylation.

Copper-catalysed bromoalkynylation of arynes

Co-reporter:Takami Morishita, Hiroto Yoshida and Joji Ohshita

Chemical Communications 2010 - vol. 46(Issue 4) pp:NaN642-642

Publication Date(Web):2009/11/18

DOI:10.1039/B919301D

Arynes were found to be inserted into a C(sp)–Br σ-bond of bromoalkynes in the presence of a copper catalyst, giving (alkynyl)bromoarenes in a straightforward manner.

Inverse regioselectivity in the silylstannylation of alkynes and allenes: copper-catalyzed three-component coupling with a silylborane and a tin alkoxide

Co-reporter:H. Yoshida, Y. Hayashi, Y. Ito and K. Takaki

Chemical Communications 2015 - vol. 51(Issue 46) pp:NaN9442-9442

Publication Date(Web):2015/04/14

DOI:10.1039/C5CC01856K

Straightforward construction of diarylmethane skeletons via aryne insertion into carbon–carbon σ-bonds

Co-reporter:Hiroto Yoshida, Masahiko Watanabe, Takami Morishita, Joji Ohshita and Atsutaka Kunai

Chemical Communications 2007(Issue 15) pp:NaN1507-1507

Publication Date(Web):2007/02/05

DOI:10.1039/B616768C

Two molar amounts of arynes were found to couple with nitriles via carbon–carbon σ-bond cleavage, assembling diverse diarylmethane skeletons in a straightforward manner.

Insertion of arynes into carbon–halogen σ-bonds: regioselective acylation of aromatic rings

Co-reporter:Hiroto Yoshida, Yasuhiro Mimura, Joji Ohshita and Atsutaka Kunai

Chemical Communications 2007(Issue 23) pp:NaN2407-2407

Publication Date(Web):2007/03/09

DOI:10.1039/B701581J

Arynes were found to insert into carbon–halogen σ-bonds of various acid halides, enabling acyl and halogen moieties to be introduced simultaneously into adjacent positions of aromatic rings.

Fluorenes as new molecular scaffolds for carbon–carbon σ-bond cleavage reaction: acylfluorenylation of arynes

Co-reporter:Hiroto Yoshida, Takeshi Kishida, Masahiko Watanabe and Joji Ohshita

Chemical Communications 2008(Issue 45) pp:NaN5965-5965

Publication Date(Web):2008/10/08

DOI:10.1039/B814597K

Acyl and fluorenyl moieties are facilely installed into neighbouring positions of aromatic skeletons via C–C bond cleavage reaction using arynes.