Hao Guo

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Name: 郭浩; Hao Guo

Organization: Fudan University , China

Department: Department of Chemistry

Title: Associate Researcher/Professor(PhD)

TOPICS

Polymer

Stimuli Responsive Polymers Stimuli Responsive Polymers Photo Responsive Polymers

Organic Chemistry

Asymmetric Synthesis allene

Chemicals
References

Synthetic applications of vinyl cyclopropane opening

Co-reporter:Marta Meazza;Ramon Rios

Organic & Biomolecular Chemistry 2017 vol. 15(Issue 12) pp:2479-2490

Publication Date(Web):2017/03/22

DOI:10.1039/C6OB02647H

Vinyl cyclopropanes are amongst the most useful building blocks in organic synthesis. Their easy opening and capacity to generate dipoles have been exploited for the synthesis of cyclopentanes with good yields and sometimes excellent stereoselectivities. In this review we give an overview of their applications, focusing on the present century.

PDMAEMA-b-PPOA-b-PDMAEMA double-bond-containing amphiphilic triblock copolymer: synthesis, characterization, and pH-responsive self-assembly

Co-reporter:Aishun Ding;Guolin Lu;Xiaoyu Huang

Polymer Chemistry (2010-Present) 2017 vol. 8(Issue 43) pp:6628-6635

Publication Date(Web):2017/11/07

DOI:10.1039/C7PY01640A

A series of ABA amphiphilic triblock copolymers consisting of hydrophobic double-bond-containing poly(phenoxyallene) (PPOA) and hydrophilic poly(2-(dimethylamino)ethyl methacrylate) (PDMAEMA) segments was synthesized by successive free radical polymerization and single-electron-transfer living radical polymerization (SET-LRP) via the site transformation strategy. Conventional free-radical homopolymerization of phenoxyallene with a cumulated double bond was first initiated by the azo group in a new bifunctional initiator comprising a Br-containing SET-LRP initiating group simultaneously for providing a polyallene-based macroinitiator, Br-PPOA-Br, bearing SET-LRP initiating groups at both ends. The target triblock copolymer of PDMAEMA-b-PPOA-b-PDMAEMA was then obtained by SET-LRP of DMAEMA initiated by the Br-PPOA-Br macroinitiator. Critical micelle concentration (cmc) of PDMAEMA-b-PPOA-b-PDMAEMA amphiphilic triblock copolymer in aqueous media was determined via fluorescence spectroscopy using N-phenyl-1-naphthylamine as a probe, which was dependent on pH and salinity of the aqueous solution. Furthermore, via transmission electron microscopy, PDMAEMA-b-PPOA-b-PDMAEMA amphiphilic triblock copolymers were found to self-assemble into spherical micelles in aqueous media.

Eosin Y-catalyzed photooxidation of triarylphosphines under visible light irradiation and aerobic conditions

Co-reporter:Yanbin Zhang;Cong Ye;Shijie Li;Aishun Ding;Guangxin Gu

RSC Advances (2011-Present) 2017 vol. 7(Issue 22) pp:13240-13243

Publication Date(Web):2017/02/24

DOI:10.1039/C6RA25469A

We report herein a novel method for Eosin Y-catalyzed photooxidation of triarylphosphines under visible light irradiation and aerobic conditions. This new approach employed visible light as the energy source and air as the oxidant, showing great advantages in environmental benignness and operational easiness with a wide functional group tolerance.

ATRP synthesis of polyallene-based amphiphilic triblock copolymer

Co-reporter:Aishun Ding;Guolin Lu;Xiaoyu Huang

Polymer Chemistry (2010-Present) 2017 vol. 8(Issue 45) pp:6997-7008

Publication Date(Web):2017/11/21

DOI:10.1039/C7PY01666B

A series of ABA triblock copolymers, comprising double-bond-containing poly(phenoxyallene) (PPOA) and poly(methoxymethyl methacrylate) (PMOMMA) segments, was synthesized by a combination of conventional free radical polymerization, atom transfer radical polymerization (ATRP) and the site transformation strategy. A new bifunctional initiator containing azo and Br-containing ATRP initiating groups was employed to initiate the conventional free radical homopolymerization of phenoxyallene with a cumulated double bond to give a PPOA-based macroinitiator (Br-PPOA-Br) bearing ATRP initiating groups at both ends. Next, ATRP of MOMMA was initiated by Br-PPOA-Br macroinitiator to produce PMOMMA-b-PPOA-b-PMOMMA triblock copolymers, which were subsequently hydrolyzed to afford PMAA-b-PPOA-b-PMAA amphiphilic triblock copolymers. The critical micelle concentration (cmc) of PMAA-b-PPOA-b-PMAA amphiphilic triblock copolymer in aqueous solution was determined by fluorescence probe technique and the dependence of cmc on pH was also investigated. These amphiphilic triblock copolymers self-assembled into wormlike and large compound micelles in aqueous media.

Polyallene-based amphiphilic triblock copolymer via successive free radical polymerization and ATRP

Co-reporter:Aishun Ding;Guolin Lu;Xiaoyu Huang

Polymer Chemistry (2010-Present) 2017 vol. 8(Issue 48) pp:7537-7545

Publication Date(Web):2017/12/12

DOI:10.1039/C7PY01407D

A new ABA amphiphilic triblock copolymer, comprising double-bond-containing poly(phenoxyallene) (PPOA) and poly(oligo(ethylene glycol) methyl ether methacrylate) (POEGMM) segments, was synthesized by a combination of conventional free radical polymerization, atom transfer radical polymerization (ATRP), and the site transformation strategy. A bifunctional initiator containing azo and Br-containing ATRP initiating groups was employed to initiate conventional free radical homopolymerization of phenoxyallene with a cumulated double bond to give a PPOA-based macroinitiator (Br-PPOA-Br) bearing ATRP initiating groups at both ends. Next, ATRP of OEGMM monomer was initiated by Br-PPOA-Br to provide the desired POEGMM-b-PPOA-b-POEGMM triblock copolymer. The critical micelle concentration of POEGMM-b-PPOA-b-POEGMM amphiphilic copolymer in aqueous solution was determined by fluorescence spectroscopy. The amphiphilic triblock copolymer could self-assemble into wormlike and spherical micelles in aqueous media. POEGMM-b-PPOA-b-POEGMM triblock copolymer can also be used as the stabilizer for the aqueous polymerization of styrene and methyl methacrylate.

Merging photoredox catalysis with Lewis acid catalysis: activation of carbon–carbon triple bonds

Co-reporter:Ruiwen Jin, Yiyong Chen, Wangsheng Liu, Dawen Xu, Yawei Li, Aishun Ding and Hao Guo

Chemical Communications 2016 vol. 52(Issue 64) pp:9909-9912

Publication Date(Web):11 Jul 2016

DOI:10.1039/C6CC03725A

Here, we demonstrate that merging photoredox catalysis with Lewis acid catalysis provides a fundamentally new activation mode of C–C triple bonds, to achieve the bond-forming reaction of alkynes with weak nucleophiles. Using a synergistic merger of Eosin Y and Cu(OTf)2, a highly efficient cyclization reaction of arene-ynes was developed.

Organophotocatalytic Synthesis of Phosphoramidates

Co-reporter:Marta Meazza;Agnieszka Kowalczuk;Luke Shirley;Jung Woon Yang;Ramon Rios

Advanced Synthesis & Catalysis 2016 Volume 358( Issue 5) pp:719-723

Publication Date(Web):

DOI:10.1002/adsc.201501068

Photoinduced Intramolecular Haloarylation and Hydroarylation of Alkynes

Co-reporter:Dawen Xu; Ramon Rios;Feifei Ba;Dongmei Ma;Guangxin Gu;Aishun Ding;Yunyan Kuang; Hao Guo

Asian Journal of Organic Chemistry 2016 Volume 5( Issue 8) pp:981-985

Publication Date(Web):

DOI:10.1002/ajoc.201600232

Abstract

The cleavage of the aryl C−X bond under UV-irradiation and its subsequent addition into an intramolecular alkyne moiety have been studied carefully. By simply regulating the addition of electron donor, highly chemoselective intramolecular hydroarylation and haloarylation reactions were achieved, providing efficient methods for the synthesis of 9-benzylidene-9H-fluorene and 9-(halo(phenyl)methylene)-9H-fluorene derivatives.

Neodymium-catalyzed intramolecular alkyne-hydroarylation with arenes

Co-reporter:Dawen Xu, Ruiwen Jin, Wangsheng Liu, Feifei Ba, Yawei Li, Aishun Ding, Hao Guo

Tetrahedron Letters 2016 Volume 57(Issue 29) pp:3235-3238

Publication Date(Web):20 July 2016

DOI:10.1016/j.tetlet.2016.06.053

•First lanthanide element catalyzed intramolecular hydroarylation.•Good functional group tolerance.•6-Endo-dig selectivity.A Nd(OTf)3-catalyzed alkyne-hydroarylation with arenes is reported. This reaction shows a wide range of functional group tolerance. Such a catalytic methodology enriches lanthanide element chemistry and provides a new route for synthesizing phenanthrene derivatives.

Synthesis of antitumor 3,4,6,7-tetrahydro-2H-pyrimido[1,6-c]quinazolin-2-imine derivatives via reductive dearomatization-initiated intramolecular cyclization

Co-reporter:Wei Li, Xiaotian Zhou, Yang Chen, Shunmin Guo, Feifei Ba, Wei Tian, Chao Yang, Mingping Wang, Yu Liu, Yunlong Song, Ju Zhu, Youjun Zhou, Feng Zhou, Hao Guo, Canhui Zheng

Tetrahedron 2016 Volume 72(Issue 23) pp:3185-3192

Publication Date(Web):9 June 2016

DOI:10.1016/j.tet.2016.04.036

In light of the importance of N-fused heterocycles in pharmaceuticals, there is continuing interest in research on N-fused heterocycles and their preparation. A new and efficient reductive dearomatization-initiated intramolecular cyclization reaction with a broad scope has been developed, affording 3,4,6,7-tetrahydro-2H-pyrimido[1,6-c]quinazolin-2-imine derivatives. Notably, this type of compound showed good inhibitory activity against specific kinases and human cancer cell lines. These results might mean a new molecular scaffold for the development of new antitumor agents.

Corrigendum to “Synthesis of antitumor 3,4,6,7-tetrahydro-2H-pyrimido[1,6-c]quinazolin-2-imine derivatives via reductive dearomatization initiated intramolecular cyclization” [Tetrahedron 72 (23) (2016) 3185–3192]

Co-reporter:Wei Li, Xiaotian Zhou, Yang Chen, Shunmin Guo, Feifei Ba, Wei Tian, Chao Yang, Mingping Wang, Yu Liu, Yunlong Song, Ju Zhu, Weicheng Zhou, Youjun Zhou, Feng Zhou, Hao Guo, Canhui Zheng

Tetrahedron 2016 Volume 72(Issue 49) pp:8123

Publication Date(Web):8 December 2016

DOI:10.1016/j.tet.2016.10.051

Cu(II)-Catalyzed 6π-Photocyclization of Dienynes

Co-reporter:Ruiwen Jin, Jinjin Chen, Yiyong Chen, Wangsheng Liu, Dawen Xu, Yawei Li, Aishun Ding, and Hao Guo

The Journal of Organic Chemistry 2016 Volume 81(Issue 24) pp:12553-12558

Publication Date(Web):November 16, 2016

DOI:10.1021/acs.joc.6b02537

The first 6π-photocyclization of dienynes was developed, which provides a new and effective protocol for the synthesis of the phenyl ring in excellent yields with nice functional group tolerance. In this transformation, the Cu(OTf)2 catalyst plays a key role in the conversion of alkyne moiety into an alkene-type moiety, which means that the dienyne reactant is converted into a triene-type substrate. Thus, this reaction proceeds via a Cu(II)-catalyzed 6π-photocyclization of triene-type derivatives.

Methyltrioxorhenium-catalyzed highly selective dihydroxylation of 1,2-allenylic diphenyl phosphine oxides

Co-reporter:Junli Hou, Yang Chen, Dongmei Ma, Burghard Cordes, Jingyun Wang, Xin Wang, Fritz E. Kühn, Hao Guo and Mingdong Zhou

Chemical Communications 2015 vol. 51(Issue 35) pp:7439-7442

Publication Date(Web):12 Mar 2015

DOI:10.1039/C5CC01160D

For the first time, methyltrioxorhenium (MTO) has been applied as a catalyst for the dihydroxylation of allenes in the presence of hydrogen peroxide as the oxidant. The regioselectivities turn out to be well controlled, affording β-carbonyl-γ-hydroxyl diphenyl phosphine oxides as the only product. The axial chirality of optically active allenes can also be nicely transferred to the chirality center of the products. Based on chirality transfer experiments and ESI-MS studies of 18O-labeled products, a possible mechanism, proceeding via regioselective epoxidation of the electron-rich carbon–carbon double bond, a subsequent intermolecular nucleophilic attack of a water molecule on the in situ formed epoxide via neighboring group participation (NGP), followed by a rearrangement has been proposed as the major reaction pathway.

Visible light induced cyclopropanation of dibromomalonates with alkenes via double-SET by photoredox catalysis

Co-reporter:Yanbin Zhang, Rong Qian, Xingliang Zheng, Yi Zeng, Jing Sun, Yiyong Chen, Aishun Ding and Hao Guo

Chemical Communications 2015 vol. 51(Issue 1) pp:54-57

Publication Date(Web):10 Nov 2014

DOI:10.1039/C4CC08203F

We report herein a visible light induced generation of a carbanion via double-SET and its application in cyclopropanation of alkenes. This new synthetic approach to form cyclopropane derivatives was conducted under mild conditions, using sunlight in open air, showing the features such as environmental benignness and an easy to handle procedure.

Photoinduced additive-free trifluoromethylation of aromatic aldehydes with TMSCF3

Co-reporter:Jing Sun, Xinhua Peng, Hao Guo

Tetrahedron Letters 2015 Volume 56(Issue 6) pp:797-800

Publication Date(Web):4 February 2015

DOI:10.1016/j.tetlet.2014.12.086

We report herein a new and effective method for additive-free trifluoromethylation of aromatic aldehydes with TMSCF3. Normal acidic hydrolysis for desilylation in the workup process is not required in this transformation. This reaction presents a new environmentally friendly protocol to access trifluoromethylated benzyl alcohols.

Studies of Free Radical Polymerization Initiated by Visible Light Photoredox Catalysis

Co-reporter:Yiyong Chen;Zhongnan Hu;Dawen Xu;Yingfeng Yu;Xiaolin Tang

Macromolecular Chemistry and Physics 2015 Volume 216( Issue 10) pp:1055-1060

Publication Date(Web):

DOI:10.1002/macp.201500006

Catalyst-free photocyclopropanation of dibromomalonates with alkenes: an approach to multisubstituted cyclopropanes

Co-reporter:Yanbin Zhang, Yong An, Jing Sun, Aishun Ding, Yu Wang, Ramon Rios, Hao Guo

Tetrahedron Letters 2015 Volume 56(Issue 46) pp:6499-6502

Publication Date(Web):18 November 2015

DOI:10.1016/j.tetlet.2015.10.012

We report herein a novel photocyclopropanation of dibromomalonates with alkenes in the presence of Hünig base. This protocol provides an environmentally benign approach for the synthesis of multisubstituted cyclopropanes, since no catalyst is required. The Photo-induced Electron Transfer (PET) from Hünig base to dibromomalonate is the key process during this transformation.We report herein a novel photocyclopropanation of dibromomalonates with alkenes in the presence of Hünig base. This protocol provides an environmentally benign approach for the synthesis of multisubstituted cyclopropanes, since no catalyst is required. The Photo-induced Electron Transfer (PET) from Hünig base to dibromomalonate is the key process during this transformation.

Reactivity Switch Enabled by Counterion: Highly Chemoselective Dimerization and Hydration of Terminal Alkynes

Co-reporter:Caixia Xu, Weiyuan Du, Yi Zeng, Bin Dai, and Hao Guo

Organic Letters 2014 Volume 16(Issue 3) pp:948-951

Publication Date(Web):January 27, 2014

DOI:10.1021/ol403684a

A counterion-controlled reactivity tuning in Pd-catalyzed highly chemoselective and regioselective dimerization and hydration of terminal alkynes is reported. The use of acetate as counterion favors the formation of an alkenyl alkynyl palladium intermediate which forms hitherto less reported 1,3-diaryl-substituted conjugated enynes after reductive elimination. Using chloride, which is a better leaving group, leads to anion exchange on the alkenylpalladium intermediate with hydroxide which after reductive elimination and tautomerization delivered the hydration products.

Synthesis of α-di or trisubstituted (tetrahydrofuran-2-yl)methanols via photoinduced additive-free intermolecular addition of THF to aromatic aldehydes or ketones

Co-reporter:Xinqi Hao, Chaoli Liu, Chenli Liu, Yiyong Chen, Xuemei Zhao, Maoping Song, Rong Qian, Hao Guo

Tetrahedron Letters 2013 Volume 54(Issue 50) pp:6964-6966

Publication Date(Web):11 December 2013

DOI:10.1016/j.tetlet.2013.10.063

THF is found to react with aromatic aldehydes or ketones highly chemoselectively under the irradiation of ultraviolet without any additives, which provides a new protocol to access α-di or trisubstituted (tetrahydrofuran-2-yl)methanols. The scope of this reaction is well studied.THF is found to react with aromatic aldehydes or ketones highly chemoselectively under the irradiation of ultraviolet without any additives, which provides a new protocol to access α-di or trisubstituted (tetrahydrofuran-2-yl)methanols. The scope of this reaction is well studied.

Synthesis of PMHDO-g-PDEAEA well-defined amphiphilic graft copolymer via successive living coordination polymerization and SET-LRP

Co-reporter:Guolin Lu;Yongjun Li;Hongsheng Gao;Xingliang Zheng;Xiaoyu Huang

Journal of Polymer Science Part A: Polymer Chemistry 2013 Volume 51( Issue 5) pp:1099-1106

Publication Date(Web):

DOI:10.1002/pola.26470

Abstract

A series of well-defined amphiphilic graft copolymer containing hydrophobic polyallene-based backbone and hydrophilic poly(2-(diethylamino)ethyl acrylate) (PDEAEA) side chains was synthesized by sequential living coordination polymerization of 6-methyl-1,2-heptadiene-4-ol (MHDO) and single electron transfer-living radical polymerization (SET-LRP) of 2-(diethylamino)ethyl acrylate (DEAEA). Ni-catalyzed living coordination polymerization of MHDO was first performed in toluene to give a well-defined double-bond-containing poly(6-methyl-1,2-heptadiene-4-ol) (PMHDO) homopolymer with a low polydispersity (M_w/M_n = 1.10). Next, 2-chloropropionyl chloride was used for the esterification of pendant hydroxyls in every repeating unit of the homopolymer so that the homopolymer was converted to PMHDO-Cl macroinitiator. Finally, SET-LRP of DEAEA was initiated by the macroinitiator in tetrahydrofuran/H₂O using CuCl/tris(2-(dimethylamino)ethyl)amine as catalytic system to afford well-defined PMHDO-g-PDEAEA graft copolymers (M_w/M_n ≤ 1.22) through the grafting-from strategy. The critical micelle concentration (cmc) was determined by ﬂuorescence spectroscopy with N-phenyl-1-naphthylamine as probe and the micellar morphology was visualized by transmission electron microscopy. © 2012 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem, 2013

SET-LRP synthesis of PMHDO-g-PNIPAM well-defined amphiphilic graft copolymer

Co-reporter:Aishun Ding;Guolin Lu;Xingliang Zheng;Xiaoyu Huang

Journal of Polymer Science Part A: Polymer Chemistry 2013 Volume 51( Issue 5) pp:1091-1098

Publication Date(Web):

DOI:10.1002/pola.26469

Abstract

A well-defined amphiphilic graft copolymer, consisting of hydrophobic polyallene-based backbone and hydrophilic poly(N-isopropylacrylamide) (PNIPAM) side chains, was prepared by the combination of living coordination polymerization, single electron transfer-living radical polymerization (SET-LRP), and the grafting-from strategy. First, the double-bond-containing backbone was prepared by [(η³-allyl)NiOCOCF₃]₂-initiated living coordination polymerization of 6-methyl-1,2-heptadiene-4-ol (MHDO). Next, the pendant hydroxyls in every repeating unit of poly(6-methyl-1,2-heptadiene-4-ol) (PMHDO) homopolymer were treated with 2-chloropropionyl chloride to give PMHDO-Cl macroinitiator. Finally, PNIPAM side chains were grown from PMHDO backbone via SET-LRP of N-isopropylacrylamide initiated by PMHDO-Cl macroinitiator in N,N-dimethylformamide/2-propanol using copper(I) chloride/tris(2-(dimethylamino)ethyl)amine as catalytic system to afford PMHDO-g-PNIPAM graft copolymers with a narrow molecular weight distribution (M_w/M_n = 1.19). The critical micelle concentration (cmc) in water was determined by fluorescence probe technique and the effects of pH and salinity on the cmc of PMHDO-g-PNIPAM were also investigated. The micellar morphology was found to be spheres using transmission electron microscopy. © 2012 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem, 2013

Catalyst-free photooxidation of triarylphosphines under aerobic conditions

Co-reporter:Aishun Ding, Yu Wang, Ramon Rios, Jing Sun, ... Hao Guo

Journal of Saudi Chemical Society (November 2015) Volume 19(Issue 6) pp:706-709

Publication Date(Web):1 November 2015

DOI:10.1016/j.jscs.2015.07.004

A new method for the photooxidation of triarylphosphines into the corresponding oxides is developed. In this new protocol, neither a catalyst nor an additive is required. The greenest oxidant, oxygen in air atmosphere, is used. After a short period of photo irradiation at rt, stoichiometric amounts of the oxides can be easily afforded by simply recycling the solvent under vacuum. No waste is formed in the whole process of this reaction. The substrate scope of this reaction is broad, showing very good application prospects in both organic chemistry and industrial processes.

Synthesis of 2,4,5-triarylated imidazoles via three-component domino reaction under catalyst-free conditions

Co-reporter:Yang Chen, Ren Wang, Feifei Ba, Junli Hou, ... Hao Guo

Journal of Saudi Chemical Society (January 2017) Volume 21(Issue 1) pp:76-81

Publication Date(Web):1 January 2017

DOI:10.1016/j.jscs.2016.03.001

A one-pot synthesis of 2,4,5-triarylated imidazoles via three-component domino reaction of 2,2-dibromo-1,2-diarylethanones, ammonium acetate, and aryl aldehydes under catalyst-free conditions is developed. The scope of this reaction is studied. A possible mechanism is proposed based on experimental results.

Correction: Novel strategies for catalytic asymmetric synthesis of C1-chiral 1,2,3,4-tetrahydroisoquinolines and 3,4-dihydrotetrahydroisoquinolines

Co-reporter:Wangsheng Liu, Shasha Liu, Ruiwen Jin, Hao Guo and Jinbo Zhao

Inorganic Chemistry Frontiers 2015 - vol. 2(Issue 4) pp:NaN446-446

Publication Date(Web):2015/02/19

DOI:10.1039/C5QO90010G

Correction for ‘Novel strategies for catalytic asymmetric synthesis of C1-chiral 1,2,3,4-tetrahydroisoquinolines and 3,4-dihydrotetrahydroisoquinolines’ by Wangsheng Liu et al., Org. Chem. Front., 2015, DOI: 10.1039/c4qo00294f.

Novel strategies for catalytic asymmetric synthesis of C1-chiral 1,2,3,4-tetrahydroisoquinolines and 3,4-dihydrotetrahydroisoquinolines

Co-reporter:Wangsheng Liu, Shasha Liu, Ruiwen Jin, Hao Guo and Jinbo Zhao

Inorganic Chemistry Frontiers 2015 - vol. 2(Issue 3) pp:NaN299-299

Publication Date(Web):2014/12/16

DOI:10.1039/C4QO00294F

1,2,3,4-Tetrahydroisoquinoline is one of the most important “privileged scaffolds” present in natural products. C1-chiral tetrahydroisoquinolines have exhibited a wide variety of bioactivities and found applications as chiral scaffolds in asymmetric catalysis. This paper summarizes novel catalytic stereoselective strategies that emerged in the last ten years for synthesis of 1,2,3,4-tetrahydroisoquinoline and 3,4-dihydroisoquinoline scaffolds, beyond the traditional Pictet–Spengler and related protocols, as well as their applications in the total synthesis of alkaloid natural products.

Synthetic applications of vinyl cyclopropane opening

Co-reporter:Marta Meazza, Hao Guo and Ramon Rios

Organic & Biomolecular Chemistry 2017 - vol. 15(Issue 12) pp:NaN2490-2490

Publication Date(Web):2017/02/20

DOI:10.1039/C6OB02647H

CuBr2-promoted cyclization and bromination of arene–alkynes: C–Br bond formation via reductive elimination of Cu(III) species

Co-reporter:Wangsheng Liu, Jinjin Chen, Ruiwen Jin, Dawen Xu, Yawei Li, Feifei Ba, Guangxin Gu, Yunyan Kuang and Hao Guo

Inorganic Chemistry Frontiers 2016 - vol. 3(Issue 7) pp:NaN855-855

Publication Date(Web):2016/05/13

DOI:10.1039/C6QO00117C

A CuBr2-promoted cyclization and bromination of arene–alkyne substrates has been developed, affording 9-bromophenanthrene derivatives highly efficiently. This reaction provides a novel and efficient protocol for C–Br bond formation from an inorganic bromine source via the reductive elimination of the Cu(III) species.

Light-mediated, palladium-catalyzed cyclizations of unactivated 1,6-dienes

Co-reporter:Weiyuan Du, Gangfeng Tang, Yiyong Chen, Dawen Xu and Hao Guo

Inorganic Chemistry Frontiers 2014 - vol. 1(Issue 8) pp:NaN923-923

Publication Date(Web):2014/07/15

DOI:10.1039/C4QO00145A

We report herein a light-mediated, palladium-catalyzed cyclization of unactivated 1,6-dienes under UV irradiation at rt. 1,5-Dimethylcyclopent-1-enes are formed as the only product in this transformation in moderate to excellent yields. This reaction offers a new insight into the realization of photochemical access to monocycles under ambient conditions.

Photoinduced HBr-catalyzed C–Si bond cleavage of benzylsilanes and their subsequent oxidation into benzoic acids with air as the terminal oxidant

Co-reporter:Jing Sun, Yu Wang, Liqiong Han, Dawen Xu, Yiyong Chen, Xinhua Peng and Hao Guo

Inorganic Chemistry Frontiers 2014 - vol. 1(Issue 10) pp:NaN1204-1204

Publication Date(Web):2014/10/06

DOI:10.1039/C4QO00229F

A photoinduced highly efficient C–Si bond cleavage reaction of benzylsilanes under the catalysis of HBr was developed. The in situ generated benzyl radical intermediates were aerobically oxidized into benzoic acids highly chemoselectively. In this transformation, HBr not only acted as the single electron transfer mediator for the initial C–Si bond cleavage, but also efficiently catalyzed the oxidation of benzaldehyde intermediates into benzoic acids.

Visible light induced cyclopropanation of dibromomalonates with alkenes via double-SET by photoredox catalysis

Co-reporter:Yanbin Zhang, Rong Qian, Xingliang Zheng, Yi Zeng, Jing Sun, Yiyong Chen, Aishun Ding and Hao Guo

Chemical Communications 2015 - vol. 51(Issue 1) pp:NaN57-57

Publication Date(Web):2014/11/10

DOI:10.1039/C4CC08203F

Merging photoredox catalysis with Lewis acid catalysis: activation of carbon–carbon triple bonds

Co-reporter:Ruiwen Jin, Yiyong Chen, Wangsheng Liu, Dawen Xu, Yawei Li, Aishun Ding and Hao Guo

Chemical Communications 2016 - vol. 52(Issue 64) pp:NaN9912-9912

Publication Date(Web):2016/07/11

DOI:10.1039/C6CC03725A

Methyltrioxorhenium-catalyzed highly selective dihydroxylation of 1,2-allenylic diphenyl phosphine oxides

Co-reporter:Junli Hou, Yang Chen, Dongmei Ma, Burghard Cordes, Jingyun Wang, Xin Wang, Fritz E. Kühn, Hao Guo and Mingdong Zhou