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Dive into the research topics where Guoqiang Yang is active.

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Featured researches published by Guoqiang Yang.


Journal of the American Chemical Society | 2014

Pd(II)-Catalyzed meta-C–H Olefination, Arylation, and Acetoxylation of Indolines Using a U-Shaped Template

Guoqiang Yang; Petra Lindovska; Dajian Zhu; Justin Kim; Peng Wang; Ri-Yuan Tang; Mohammad Movassaghi; Jin-Quan Yu

meta-C-H olefination, arylation, and acetoxylation of indolines have been developed using nitrile-containing templates. The combination of a monoprotected amino acid ligand and the nitrile template attached at the indolinyl nitrogen via a sulfonamide linkage is crucial for the meta-selective C-H functionalization of electron-rich indolines that are otherwise highly reactive toward electrophilic palladation at the para-positions. A wide range of synthetically important and advanced indoline analogues are selectively functionalized at the meta-positions.


Angewandte Chemie | 2013

A Palladium-Catalyzed Enantioselective Addition of Arylboronic Acids to Cyclic Ketimines†

Guoqiang Yang; Wanbin Zhang

Sly as Nicox: A palladium-catalyzed addition of arylboronic acids to ketimines has been developed to efficiently provide products in up to 99 % yield and 96 % ee. The reactions could be run under aerobic conditions and with unpurified trifluoroethanol (TFE). A pyrrolidine compound bearing a chiral α-tertiary amine was synthesized in several steps without loss of enantioselectivity. TFA = trifluoroacetate.


Angewandte Chemie | 2014

Palladium-Catalyzed Allylic Alkylation of Simple Ketones with Allylic Alcohols and Its Mechanistic Study†

Xiaohong Huo; Guoqiang Yang; Delong Liu; Yangang Liu; Ilya D. Gridnev; Wanbin Zhang

Allylic alcohols were directly used in Pd-catalyzed allylic alkylations of simple ketones under mild reaction conditions. The reaction proceeded smoothly at 20 °C by the concerted action of a Pd catalyst, a pyrrolidine co-catalyst, and a hydrogen-bonding solvent, and does not require any additional reagents. A computational study suggested that methanol plays a crucial role in the formation of the π-allylpalladium complex by lowering the activation barrier.


Angewandte Chemie | 2012

An Asymmetric Aerobic Aza-Wacker-Type Cyclization: Synthesis of Isoindolinones Bearing Tetrasubstituted Carbon Stereocenters†

Guoqiang Yang; Chaoren Shen; Wanbin Zhang

Its all in the solvent: An enantioselective variant of an aza-Wacker-type cyclization that gives isoindolinones containing tetrasubstituted carbon centers α to the nitrogen atom has been developed (see scheme; tfa=trifluoroacetate). The use of a highly coordinating solvent is crucial for the activity of the catalyst and the stereoselectivity the reaction (up to 99 % ee).


Angewandte Chemie | 2015

Ligand-Promotedortho-CH Amination with Pd Catalysts

Dajian Zhu; Guoqiang Yang; Jian He; Ling Chu; Gang Chen; Wei Gong; Ke Chen; Martin D. Eastgate; Jin-Quan Yu

2,4,6-Trimethoxypyridine is identified as an efficient ligand for promoting a Pd-catalyzed ortho-C-H amination of both benzamides and triflyl-protected benzylamines. This finding provides guidance for the development of ligands that can improve or enable Pd(II)-catalyzed Csp2-H activation reactions directed by weakly coordinating functional groups.


Organic Letters | 2014

Hydrogen-Bond-Activated Palladium-Catalyzed Allylic Alkylation via Allylic Alkyl Ethers: Challenging Leaving Groups

Xiaohong Huo; Mao Quan; Guoqiang Yang; Xiaohu Zhao; Delong Liu; Yangang Liu; Wanbin Zhang

C-O bond cleavage of allylic alkyl ether was realized in a Pd-catalyzed hydrogen-bond-activated allylic alkylation using only alcohol solvents. This procedure does not require any additives and proceeds with high regioselectivity. The applicability of this transformation to a variety of functionalized allylic ether substrates was also investigated. Furthermore, this methodology can be easily extended to the asymmetric synthesis of enantiopure products (99% ee).


Organic Letters | 2012

Regioselective Pd-catalyzed aerobic aza-Wacker cyclization for preparation of isoindolinones and isoquinolin-1(2H)-ones.

Guoqiang Yang; Wanbin Zhang

A switchable regioselective intramolecular aerobic aza-Wacker cyclization catalyzed by palladium is presented. Isoindolinones or isoquinolin-1(2H)-ones could be prepared selectively from the same substrates using different catalysts. The type and steric hindrance of the ligands may be the variables most significant for regiocontrol.


Organic Letters | 2016

Pd(II)-Catalyzed Asymmetric Addition of Arylboronic Acids to Isatin-Derived Ketimines

Qun He; Liang Wu; Xuezhen Kou; Nicholas Butt; Guoqiang Yang; Wanbin Zhang

A Pd(II)/Pyrox-catalyzed enantioselecitve addition of arylboronic acids to 3-ketimino oxindoles was developed, providing chiral 3-amino-2-oxindoles with a quaternary stereocenter in high yields and with good enantioselectivities. A variety of functionalized 3-ketimino oxindoles can be used, and the method tolerates some variation in arylboronic acid scope. This asymmetric arylation provides an alternative efficient catalytic method for the preparation of chiral 3-aryl-3-amino-2-oxindoles, which also represents the first example of a Pd(II)-catalyzed addition of arylborons to exocyclic ketimines.


Organic chemistry frontiers | 2015

Pd(II)-catalyzed asymmetric addition of arylboronic acids to cyclic N-sulfonyl ketimine esters and a DFT study of its mechanism

Mao Quan; Guoqiang Yang; Fang Xie; Ilya D. Gridnev; Wanbin Zhang

A palladium-catalyzed asymmetric arylation of cyclic N-sulfonyl ketimine esters is described. The desired products could be prepared with excellent yields (up to 99%) and enantioselectivities (up to 99% ee) under mild reaction conditions. Furthermore, a possible reaction mechanism was determined using DFT calculations.


Organic Letters | 2013

Insertion of Arynes into Arylphosphoryl Amide Bonds: One-Step Simultaneous Construction of C–N and C–P Bonds

Chaoren Shen; Guoqiang Yang; Wanbin Zhang

The insertion of arynes into arylphosphoryl amide bonds to synchronously construct C-P and C-N bonds is described. Arynes generated in situ from o-triflate arylsilanes under fluoride-promoted conditions insert into relatively inert P-N bonds, producing o-amine-substituted arylphosphine oxides. This process provides a simple pathway for the preparation of precursors for a number of bidentate aminophosphine ligands.

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Wanbin Zhang

Shanghai Jiao Tong University

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Liang Wu

Zhejiang University of Technology

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Mao Quan

Shanghai Jiao Tong University

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Chaoren Shen

Shanghai Jiao Tong University

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Fang Xie

Shanghai Jiao Tong University

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Jingzhao Xia

Shanghai Jiao Tong University

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Yangang Liu

Shanghai Jiao Tong University

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Qihang Shao

Shanghai Jiao Tong University

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Xuezhen Kou

Shanghai Jiao Tong University

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