Zhan Lu

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Name: 陆展; Lu, Zhan

Organization: Zhejiang University , China

Department: Department of Chemistry

Title: Professor(PhD)

Chemicals
References

Iron-Catalyzed Hydroboration of Vinylcyclopropanes

Co-reporter:Chenhui Chen, Xuzhong Shen, Jianhui Chen, Xin Hong, and Zhan Lu

Organic Letters October 6, 2017 Volume 19(Issue 19) pp:

Publication Date(Web):September 27, 2017

DOI:10.1021/acs.orglett.7b02691

An iron-catalyzed hydroboration of vinylcyclopropane with HBpin is first reported for the preparation of valuable homoallylic organoboronic esters. The iron catalysts enable efficient and regioselective C–C cleavage of vinylcyclopropanes, stereoselectively delivering E-alkenes with good stereospecific selectivity at an allylic position. This protocol exhibits mild conditions with good functional group tolerability. The chiral homoallylic organoboronic esters could be further converted into chiral polysubstituted tetrahydrofuran and tetrahydropyran.

Intermolecular [2 + 2] Cycloaddition of 1,4-Dihydropyridines with Olefins via Energy Transfer

Co-reporter:Chengfeng Wang and Zhan Lu

Organic Letters November 3, 2017 Volume 19(Issue 21) pp:5888-5888

Publication Date(Web):October 19, 2017

DOI:10.1021/acs.orglett.7b02881

A highly regio- and diastereoselective visible-light-promoted [2 + 2] cycloaddition between readily available 1,4-dihydropyridines and olefins has been developed. This strategy is operationally simple and atom-economical and enables the construction of strained polysubstituted 2-azabicyclo[4.2.0]octanes with three all-carbon quaternary centers with good functional group tolerance. These products can be easily converted to various structurally unique derivatives. The primary mechanistic studies demonstrated that the reaction proceeds through an energy transfer pathway.

Cobalt-Catalyzed Asymmetric Sequential Hydroboration/Hydrogenation of Internal Alkynes

Co-reporter:Jun Guo, Biao Cheng, Xuzhong Shen, and Zhan Lu

Journal of the American Chemical Society November 1, 2017 Volume 139(Issue 43) pp:15316-15316

Publication Date(Web):October 18, 2017

DOI:10.1021/jacs.7b09832

A highly regio- and enantioselective cobalt-catalyzed hydroboration/hydrogenation of internal alkynes with HBpin and a hydrogen balloon in one pot was developed. A new type of chiral imidazoline iminopyridine (IIP) ligand was introduced for the first time in this novel and efficient strategy. This protocol used relatively simple and available starting materials with good functional group tolerance to construct more valuable chiral secondary organoboronates. The primary mechanistic studies illustrated that the cobalt-catalyzed regioselective hydroboration of alkynes did initially occur followed by HBpin-promoted and cobalt-catalyzed enantioselective hydrogenation of alkenylboronates.

Cobalt-Catalyzed Ligand-Controlled Regioselective Hydroboration/Cyclization of 1,6-Enynes

Co-reporter:Tuo Xi and Zhan Lu

ACS Catalysis February 3, 2017 Volume 7(Issue 2) pp:1181-1181

Publication Date(Web):December 1, 2016

DOI:10.1021/acscatal.6b02816

A ligand-controlled cobalt-catalyzed regioselective hydroboration/cyclization of 1,6-enynes with HBPin was developed by switching the size of the coordinated side arm to afford alkenylboronates and alkylboronates, respectively. Gram-scale reactions could be easily conducted, which is beneficial for further derivatizations. A primary mechanism was proposed on the basis of substrate-controlled experiments and deuterium experiments.Keywords: 1,6-enynes; cobalt-catalyzed; cyclization; hydroboration; ligand-controlled;

Visible-Light-Promoted Metal-Free Aerobic Hydroxyazidation of Alkenes

Co-reporter:Bo Yang and Zhan Lu

ACS Catalysis December 1, 2017 Volume 7(Issue 12) pp:8362-8362

Publication Date(Web):October 30, 2017

DOI:10.1021/acscatal.7b02892

A highly efficient visible-light-promoted metal-free aerobic hydroxyazidation of alkenes has been developed. This protocol was operationally simple with broad substrate scope using relatively simple and readily available starting materials, such as alkenes and air, to construct valuable β-azido alcohols which are significant building blocks to build N-containing compounds. The distinct possible mechanisms were proposed via the generation of azido radical and alkene radical cation.Keywords: alkenes; hydroxyazidation; metal-free; visible light;

Visible light-promoted dihydroxylation of styrenes with water and dioxygen

Co-reporter:Bo Yang

Chemical Communications 2017 vol. 53(Issue 94) pp:12634-12637

Publication Date(Web):2017/11/23

DOI:10.1039/C7CC06745C

An efficient visible light promoted metal-free dihydroxylation of styrenes with water and dioxygen has been developed for the construction of vicinal alcohols. The protocol was operationally simple with a broad substrate scope. The mechanistic studies demonstrated that one of the hydroxyl groups came from water and the other one came from molecular oxygen. Additionally, the β-alkyoxy alcohols could also be obtained using a similar strategy.

Recent advances in chiral imino-containing ligands for metal-catalyzed asymmetric transformations

Co-reporter:Xu Chen

Organic & Biomolecular Chemistry 2017 vol. 15(Issue 11) pp:2280-2306

Publication Date(Web):2017/03/15

DOI:10.1039/C6OB02817A

In this review, the recent applications of a variety of chiral imino-containing ligands classified by different types of metal-catalyzed asymmetric reactions are summarized. The progress made in this area would encourage us to design and synthesize more novel chiral imino-containing ligands, and explore their applications in metal-catalyzed asymmetric transformations.

Iron-Catalyzed, Markovnikov-Selective Hydroboration of Styrenes

Co-reporter:Xu Chen, Zhaoyang Cheng, and Zhan Lu

Organic Letters 2017 Volume 19(Issue 5) pp:

Publication Date(Web):February 21, 2017

DOI:10.1021/acs.orglett.7b00227

A highly Markovnikov-selective, iron-catalyzed hydroboration of styrenes is reported using available oxazolinylphenyl picolinamide as the ligand to afford the branched hydroboration products with up to >50/1 b/l. This reaction is operationally simple and could be carried out in gram scale.

Dual-Stereocontrol Asymmetric Cobalt-Catalyzed Hydroboration of Sterically Hindered Styrenes

Co-reporter:Heyi Zhang and Zhan Lu

ACS Catalysis 2016 Volume 6(Issue 10) pp:6596

Publication Date(Web):August 29, 2016

DOI:10.1021/acscatal.6b02278

An oxazoline aminoisopropylpyridine (OAP) was designed and synthesized for cobalt-catalyzed asymmetric hydroboration of sterically hindered styrenes. A unique dual-stereocontrol phenomenon was observed using a rigid OIP·CoCl2 complex or a flexible OAP with CoCl2 as precatalysts, respectively. The reaction could be easily carried out on a gram scale to afford chiral alkylboronic esters which could be converted into diverse C–X (X = C, N, O) bond cross-coupling products. The mechanistically distinct pathways were proposed on the basis of deuterium experiments.Keywords: alkenes; cobalt-catalyzed; dual stereocontrol; hydroboration; ligand design

Cobalt-Catalyzed Asymmetric Hydrogenation of 1,1-Diarylethenes

Co-reporter:Jianhui Chen, Chenhui Chen, Chonglei Ji, and Zhan Lu

Organic Letters 2016 Volume 18(Issue 7) pp:1594-1597

Publication Date(Web):March 14, 2016

DOI:10.1021/acs.orglett.6b00453

Highly enantioselective cobalt-catalyzed hydrogenation of 1,1-diarylethenes was developed by using bench-stable chiral oxazoline iminopyridine–cobalt complexes as precatalysts. A unique o-chloride effect was observed to achieve high enantioselectivity. Easy removal as well as further transformations of the chloro group make this protocol a potentially useful alternative to synthesize various chiral 1,1-diarylethanes. This process can be successfully performed under 1 atm of hydrogen at room temperature on gram scale.

Iminophenyl Oxazolinylphenylamine for Enantioselective Cobalt-Catalyzed Hydrosilylation of Aryl Ketones

Co-reporter:Xu Chen and Zhan Lu

Organic Letters 2016 Volume 18(Issue 18) pp:4658-4661

Publication Date(Web):August 30, 2016

DOI:10.1021/acs.orglett.6b02260

A new family of chiral iminophenyl oxazolinylphenylamines (IPOPA) was designed and synthesized through three steps from commercially available starting materials. An efficient cobalt-catalyzed asymmetric hydrosilylation of simple ketones with a low catalyst loading of CoCl2 and IPOPA was developed to afford chiral alcohols in good yields with high enantioselectivities.

Cobalt-Catalyzed Hydrosilylation/Cyclization of 1,6-Enynes

Co-reporter:Tuo Xi and Zhan Lu

The Journal of Organic Chemistry 2016 Volume 81(Issue 19) pp:8858-8866

Publication Date(Web):September 1, 2016

DOI:10.1021/acs.joc.6b01555

An iminopyridine cobalt dichloride complex was synthesized and demonstrated as an effective precatalyst for hydrosilylation/cyclization of 1,6-enynes with silanes. Various functional groups such as amine, free aniline, ester, ether, cyano, halide, trifluoromethyl, and heterocycle were tolerated to afford a variety of silicon-containing compounds. The reaction could be scaled up to afford products on the gram scale which could undergo further derivatizations. A primary mechanism was proposed based on analysis of side products and a deuterated experiment.

Visible-Light-Promoted Oxidative [4 + 2] Cycloadditions of Aryl Silyl Enol Ethers

Co-reporter:Bo Yang and Zhan Lu

The Journal of Organic Chemistry 2016 Volume 81(Issue 16) pp:7288-7300

Publication Date(Web):July 8, 2016

DOI:10.1021/acs.joc.6b01016

Visible-light-promoted oxidative [4 + 2] cycloadditions of ε,3-unsaturated silyl enol ethers have been developed to efficiently and diastereoselectively construct polycyclic skeletons under mild conditions. The diastereoselectivities were dependent on the stereoconfiguration of silyl enol ether, substitutions on the link, as well as electric properties of substitutions on aryl rings. The intermediates could be trapped by TEMPO, oxygen or methanol. Mechanistic studies indicated the reaction was initiated by one-electron oxidation of the silyl enol ether.

Cobalt-catalyzed asymmetric hydroboration of aryl ketones with pinacolborane

Co-reporter:Jun Guo, Jianhui Chen and Zhan Lu

Chemical Communications 2015 vol. 51(Issue 26) pp:5725-5727

Publication Date(Web):20 Feb 2015

DOI:10.1039/C5CC01084E

The highly enantioselective cobalt-catalyzed hydroboration reaction of aryl ketones with HBpin was developed using iminopyridine oxazoline ligands. Halides, amines, ethers, sulfides, esters and amides are well tolerated under the mild reaction conditions, demonstrating its synthetic advantage. Substituted diaryl ketones could also be hydroborated with high enantioselectivity.

Palladium-Catalyzed C-2 C–H Heteroarylation of Chiral Oxazolines: Diverse Synthesis of Chiral Oxazoline Ligands

Co-reporter:Tuo Xi, Yuncai Mei, and Zhan Lu

Organic Letters 2015 Volume 17(Issue 24) pp:5939-5941

Publication Date(Web):November 25, 2015

DOI:10.1021/acs.orglett.5b03041

A direct, efficient, and practical protocol to install a chiral oxazoline unit onto aryl/heteroaryl rings via palladium-catalyzed C–H functionalization of 2-positions of oxazolines with a variety of halides using dppe as the ligand has been developed. Various chiral oxazoline ligands could be synthesized, even in a 10-g scale process. This protocol is a good supplement to traditional methods and for diverse synthesis of chiral oxazoline ligands.

[3+2] Redox-Neutral Cycloaddition of Nitrocyclopropanes with Styrenes by Visible-Light Photocatalysis

Co-reporter:Chengfeng Wang;Xiang Ren; Hujun Xie; Zhan Lu

Chemistry - A European Journal 2015 Volume 21( Issue 27) pp:9676-9680

Publication Date(Web):

DOI:10.1002/chem.201500873

Abstract

The first nitro-group-initiated redox-neutral [3+2] cycloaddition of nitrocyclopropanes with alkenes by using visible-light-absorbing transition-metal complexes was reported. High diastereoselectivities were observed for two quaternary carbon centers on the ring and validated by DFT calculations. Spiro- or polycyclic structures can be constructed smoothly. Cyclic γ-amino acid derivatives and polysubstituted cyclic amino alcohols can be obtained easily through reduction of the nitro group.

Iron-Catalyzed Asymmetric Hydrosilylation of 1,1-Disubstituted Alkenes

Co-reporter:Jianhui Chen;Biao Cheng;Minyi Cao ; Zhan Lu

Angewandte Chemie 2015 Volume 127( Issue 15) pp:4744-4747

Publication Date(Web):

DOI:10.1002/ange.201411884

Abstract

The highly regio- and enantioselective iron-catalyzed anti-Markovnikov hydrosilylation of 1,1-disubstituted aryl alkenes was developed using iminopyridine oxazoline ligands to afford chiral organosilanes. Additional derivatization of these products lead to chiral organosilanols, cyclic silanes, phenol derivatives, and 3-substituted 2,3-dihydrobenzofurans.

Iron-Catalyzed Asymmetric Hydrosilylation of 1,1-Disubstituted Alkenes

Co-reporter:Jianhui Chen;Biao Cheng;Minyi Cao ; Zhan Lu

Angewandte Chemie International Edition 2015 Volume 54( Issue 15) pp:4661-4664

Publication Date(Web):

DOI:10.1002/anie.201411884

Abstract

Iminopyridine Oxazoline Iron Catalyst for Asymmetric Hydroboration of 1,1-Disubtituted Aryl Alkenes

Co-reporter:Jianhui Chen, Tuo Xi, and Zhan Lu

Organic Letters 2014 Volume 16(Issue 24) pp:6452-6455

Publication Date(Web):December 1, 2014

DOI:10.1021/ol503282r

The highly regio- and enantioselective iron-catalyzed anti-Markovnikov hydroboration of 1,1-disubstituted aryl alkenes is reported by using a novel chiral iminopyridine oxazoline (IPO) ligand, in which the iminopyridine group is proposed to stabilize the iron and chiral oxazoline group to control enantioselectivity. This distinct class of reactive IPO ligands will likely be of high value for a large variety of asymmetric transformations using first-row transition metals.

Recent advances in chiral imino-containing ligands for metal-catalyzed asymmetric transformations

Co-reporter:Xu Chen and Zhan Lu

Organic & Biomolecular Chemistry 2017 - vol. 15(Issue 11) pp:NaN2306-2306

Publication Date(Web):2017/02/13

DOI:10.1039/C6OB02817A

Catalytic enantioselective organic transformations via visible light photocatalysis

Co-reporter:Chengfeng Wang and Zhan Lu

Inorganic Chemistry Frontiers 2015 - vol. 2(Issue 2) pp:NaN190-190

Publication Date(Web):2014/12/10

DOI:10.1039/C4QO00306C

In this minireview, catalytic enantioselective transformations via visible light photocatalysis are discussed. High enantioselectivities are achieved from the combination of visible light photocatalysis with chiral organocatalysts. Considering the huge progress made in both asymmetric synthetic chemistry and visible light photocatalysis chemistry, more new chiral catalysts with varieties of transition-metals will be developed and engaged in the field of asymmetric photoreactions.

Asymmetric cobalt catalysts for hydroboration of 1,1-disubstituted alkenes

Co-reporter:Jianhui Chen, Tuo Xi, Xiang Ren, Biao Cheng, Jun Guo and Zhan Lu

Inorganic Chemistry Frontiers 2014 - vol. 1(Issue 11) pp:NaN1309-1309

Publication Date(Web):2014/11/19

DOI:10.1039/C4QO00295D

Chiral iminopyridine oxazoline (IPO) ligands were designed, synthesized and utilized for the first cobalt-catalyzed highly regio- and enantioselective anti-Markovnikov hydroboration of 1,1-disubstituted aryl alkenes. These novel IPO ligands will likely be of high value for asymmetric transformations with first-row transition metals.

Cobalt-catalyzed asymmetric hydroboration of aryl ketones with pinacolborane

Co-reporter:Jun Guo, Jianhui Chen and Zhan Lu

Chemical Communications 2015 - vol. 51(Issue 26) pp:NaN5727-5727

Publication Date(Web):2015/02/20

DOI:10.1039/C5CC01084E