Wei-Liang Duan

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Name: 段伟良; Duan, WeiLiang

Organization: Chinese Academy of Sciences , China

Department: Shanghai Institute of Organic Chemistry

Title: Researcher(PhD)

TOPICS

Organic Chemistry

Asymmetric Synthesis C-H Activation

Chemicals
References

Palladium-Catalyzed Asymmetric Arylation of C(sp3)–H Bonds of Aliphatic Amides: Controlling Enantioselectivity Using Chiral Phosphoric Amides/Acids

Co-reporter:Shao-Bai Yan, Song Zhang, and Wei-Liang Duan

Organic Letters 2015 Volume 17(Issue 10) pp:2458-2461

Publication Date(Web):May 4, 2015

DOI:10.1021/acs.orglett.5b00968

Enantioselective arylation of secondary β-C(sp3)–H bonds of 8-aminoquinoline amides was realized with a palladium catalyst. Chiral phosphoric amides and acids were used for the first time to control the stereoselectivity at the C–H bond cleavage step in the C–H activation reactions.

Palladium-Catalyzed Enantioselective CH Arylation for the Synthesis of P-Stereogenic Compounds

Co-reporter:Zi-Qi Lin;Wei-Zhen Wang;Shao-Bai Yan ;Dr. Wei-Liang Duan

Angewandte Chemie 2015 Volume 127( Issue 21) pp:6363-6367

Publication Date(Web):

DOI:10.1002/ange.201500201

Abstract

A palladium-catalyzed enantioselective CH arylation of N-(o-bromoaryl)-diarylphosphinic amides is described for the synthesis of phosphorus compounds bearing a P-stereogenic center. The method provides good enantioselectivities and high yields. The products were readily transformed into P-chiral biphenyl monophosphine ligands.

Palladium-Catalyzed Enantioselective CH Arylation for the Synthesis of P-Stereogenic Compounds

Co-reporter:Zi-Qi Lin;Wei-Zhen Wang;Shao-Bai Yan ;Dr. Wei-Liang Duan

Angewandte Chemie International Edition 2015 Volume 54( Issue 21) pp:6265-6269

Publication Date(Web):

DOI:10.1002/anie.201500201

Abstract

Palladium-catalyzed asymmetric 1,6-addition of diarylphosphines to α,β,γ,δ-unsaturated sulfonic esters: controlling regioselectivity by rational selection of electron-withdrawing groups

Co-reporter:Junzhu Lu, Jinxing Ye and Wei-Liang Duan

Chemical Communications 2014 vol. 50(Issue 6) pp:698-700

Publication Date(Web):11 Nov 2013

DOI:10.1039/C3CC46290K

Palladium-catalyzed asymmetric 1,6-addition of diarylphosphines to electron-deficient dienes was developed through rational selection of electron-withdrawing groups on the dienes. Various chiral allylic phosphine derivatives were synthesized in good yields with high enantioselectivity (up to 96% ee).

2-Hydroxy-1,10-phenanthroline vs 1,10-Phenanthroline: Significant Ligand Acceleration Effects in the Palladium-Catalyzed Oxidative Heck Reaction of Arenes

Co-reporter:Cheng-Hao Ying, Shao-Bai Yan, and Wei-Liang Duan

Organic Letters 2014 Volume 16(Issue 2) pp:500-503

Publication Date(Web):December 30, 2013

DOI:10.1021/ol4033804

A series of bidentate monoanionic nitrogen ligands were designed and applied in the Pd-catalyzed oxidative Heck reaction of arenes with alkenes. Significant ligand-accelerated effects were observed, and direct C–H functionalized products were formed in high yields with meta-selectivity.

Palladium-catalyzed asymmetric 1,6-addition of diphenylphosphine to (4-aryl-1,3-butadienylidene)bis(phosphonates) for the synthesis of chiral phosphines

Co-reporter:Jian Huang, Mei-Xin Zhao, Wei-Liang Duan

Tetrahedron Letters 2014 Volume 55(Issue 3) pp:629-631

Publication Date(Web):15 January 2014

DOI:10.1016/j.tetlet.2013.11.086

An asymmetric 1,6-addition of diphenylphosphine to (4-aryl-1,3-butadienylidene)bis(phosphonates) catalyzed by a PCP pincer–Pd complex has been developed for the synthesis of chiral allylic phosphines with up to 91% ee under mild conditions.

NHC–copper-catalyzed asymmetric 1,4-addition of diarylphosphines to α,β-unsaturated ketones

Co-reporter:Yun-Rong Chen, Jian-Jun Feng, Wei-Liang Duan

Tetrahedron Letters 2014 Volume 55(Issue 3) pp:595-597

Publication Date(Web):15 January 2014

DOI:10.1016/j.tetlet.2013.10.158

N-Heterocyclic carbene–copper-catalyzed asymmetric 1,4-addition of diarylphosphines to α,β-unsaturated ketones was developed for the synthesis of chiral phosphorus derivatives in high yields with moderate enantioselectivity under mild conditions.

Silver-Mediated Oxidative C–H/P–H Functionalization: An Efficient Route for the Synthesis of Benzo[b]phosphole Oxides

Co-reporter:Yun-Rong Chen

Journal of the American Chemical Society 2013 Volume 135(Issue 45) pp:16754-16757

Publication Date(Web):October 28, 2013

DOI:10.1021/ja407373g

A Ag-mediated C–H/P–H functionalization reaction of arylphosphine oxides with internal alkynes was described for the direct preparation of benzo[b]phosphole oxides with a high yield. An unusual aryl migration on the P-atom derived from a C–P bond cleavage and a new C–P bond formation was also observed and demonstrated to proceed via the radical process.

Palladium-Catalyzed Asymmetric Addition of Diarylphosphines to α,β-Unsaturated Sulfonic Esters for the Synthesis of Chiral Phosphine Sulfonate Compounds

Co-reporter:Junzhu Lu, Jinxing Ye, and Wei-Liang Duan

Organic Letters 2013 Volume 15(Issue 19) pp:5016-5019

Publication Date(Web):September 19, 2013

DOI:10.1021/ol402351c

Highly stereoselective addition of diarylphosphines to α,β-unsaturated sulfonic esters catalyzed through a PCP pincer–Pd complex is developed to synthesize chiral phosphine sulfonic esters with excellent enantioselectivity (up to 99.5% ee). The transformation of the chiral adduct into a useful palladium phosphine sulfonate complex is also demonstrated.

Palladium-catalyzed Asymmetric 1,4-Addition of Diarylphosphines to ,-Unsaturated Carboxylic Esters

Co-reporter:Dan Du;Zi-Qi Lin;Jun-Zhu Lu;Chun Li;Dr. Wei-Liang Duan

Asian Journal of Organic Chemistry 2013 Volume 2( Issue 5) pp:392-394

Publication Date(Web):

DOI:10.1002/ajoc.201300021

Palladium-catalyzed asymmetric addition of diarylphosphines to N-tosylimines

Co-reporter:Miao Huang, Chun Li, Jian Huang, Wei-Liang Duan and Sheng Xu

Chemical Communications 2012 vol. 48(Issue 90) pp:11148-11150

Publication Date(Web):26 Sep 2012

DOI:10.1039/C2CC35563A

Bis(phosphine) pincer–Pd complex-catalyzed asymmetric addition of diarylphosphines to N-tosylimines was developed for the synthesis of chiral phosphine sulfides with high stereoselectivities (up to 96% ee) under mild conditions.

Palladium-Catalyzed Asymmetric 1,4-Addition of Diarylphosphines to Nitroalkenes for the Synthesis of Chiral P,N-Compounds

Co-reporter:Jian-Jun Feng;Miao Huang;Zi-Qi Lin

Advanced Synthesis & Catalysis 2012 Volume 354( Issue 16) pp:3122-3126

Publication Date(Web):

DOI:10.1002/adsc.201200133

Abstract

A highly stereoselective asymmetric 1,4-addition of diarylphosphines to nitroalkenes catalyzed by a bis(phosphine) pincer-palladium complex has been developed for the synthesis of chiral P,N compounds with good to excellent enantioselectivities (up to 94% ee) under mild conditions.

Palladium-catalyzed 1,4-addition of diarylphosphines to α,β-unsaturated N-acylpyrroles

Co-reporter:Dan Du and Wei-Liang Duan

Chemical Communications 2011 vol. 47(Issue 39) pp:11101-11103

Publication Date(Web):12 Sep 2011

DOI:10.1039/C1CC13785A

Highly stereoselective asymmetric 1,4-addition of diarylphosphines to α,β-unsaturated N-acylpyrroles catalyzed by a PCP pincer–Pd complex has been developed for the synthesis of chiral phosphines with excellent stereoselectivity (91–99% ee) under mild conditions. The products obtained can be further converted into chiral phosphine-oxazoline ligands.

Palladium-Catalyzed 1,4-Addition of Diarylphosphines to α,β-Unsaturated Aldehydes

Co-reporter:Yun-Rong Chen and Wei-Liang Duan

Organic Letters 2011 Volume 13(Issue 21) pp:5824-5826

Publication Date(Web):October 6, 2011

DOI:10.1021/ol2024339

A highly stereoselective asymmetric 1,4-addition of diarylphosphines to α,β-unsaturated aldehydes catalyzed by a bis(phosphine) pincer–Pd complex has been developed for the synthesis of chiral phosphines with excellent stereoselectivity (up to 98% ee) under mild conditions. The application of the current method to the synthesis of enantiopure bisphosphine and its pincer–Pd complex has also been demonstrated.

Palladium-Catalyzed Asymmetric Addition of Diarylphosphines to Enones toward the Synthesis of Chiral Phosphines

Co-reporter:Jian-Jun Feng ; Xue-Feng Chen ; Min Shi

Journal of the American Chemical Society 2010 Volume 132(Issue 16) pp:5562-5563

Publication Date(Web):April 1, 2010

DOI:10.1021/ja100606v

An asymmetric addition of diarylphosphines to β-substituted enones under mild conditions using a chiral pincer−palladium catalyst has been developed for the synthesis of chiral phosphines with excellent stereoselectivity (up to 99% ee).

Palladium-catalyzed 1,4-addition of secondary alkylphenylphosphines to α,β-unsaturated carbonyl compounds for the synthesis of phosphorus- and carbon-stereogenic compounds

Co-reporter:Chun Li, Qing-Long Bian, Sheng Xu and Wei-Liang Duan

Inorganic Chemistry Frontiers 2014 - vol. 1(Issue 5) pp:NaN545-545

Publication Date(Web):2014/04/21

DOI:10.1039/C4QO00017J

Highly stereoselective 1,4-addition of alkylphenylphosphines to α,β-unsaturated carbonyl compounds catalyzed by PCP or NCN pincer–Pd complexes is described to synthesize chiral phosphorus compounds bearing both P- and C-stereogenic centers with good to excellent enantioselectivity (up to 99.6% ee).

Palladium-catalyzed direct C–H allylation of arenes without directing groups

Co-reporter:Cheng-Hao Ying and Wei-Liang Duan

Inorganic Chemistry Frontiers 2014 - vol. 1(Issue 5) pp:NaN550-550

Publication Date(Web):2014/04/28

DOI:10.1039/C4QO00097H

A palladium-catalyzed direct C–H allylation of simple arenes without directing groups was developed for allyl arene synthesis. The use of bidentate monoanionic nitrogen ligands enabled the progress of initial C–H activation of arenes, as well as the subsequent insertion and β-OAc elimination.

Palladium-catalyzed asymmetric 1,6-addition of diarylphosphines to α,β,γ,δ-unsaturated sulfonic esters: controlling regioselectivity by rational selection of electron-withdrawing groups

Co-reporter:Junzhu Lu, Jinxing Ye and Wei-Liang Duan

Chemical Communications 2014 - vol. 50(Issue 6) pp:NaN700-700

Publication Date(Web):2013/11/11

DOI:10.1039/C3CC46290K

Palladium-catalyzed asymmetric addition of diarylphosphines to N-tosylimines

Co-reporter:Miao Huang, Chun Li, Jian Huang, Wei-Liang Duan and Sheng Xu

Chemical Communications 2012 - vol. 48(Issue 90) pp:NaN11150-11150

Publication Date(Web):2012/09/26

DOI:10.1039/C2CC35563A

Palladium-catalyzed 1,4-addition of diarylphosphines to α,β-unsaturated N-acylpyrroles

Co-reporter:Dan Du and Wei-Liang Duan