Literature DB >> 27093112

Directed, Regiocontrolled Hydroamination of Unactivated Alkenes via Protodepalladation.

John A Gurak1, Kin S Yang1, Zhen Liu1, Keary M Engle1.   

Abstract

A directed, regiocontrolled hydroamination of unactivated terminal and internal alkenes is reported. The reaction is catalyzed by palladium(II) acetate and is compatible with a variety of nitrogen nucleophiles. A removable bidentate directing group is used to control the regiochemistry, prevent β-hydride elimination, and stabilize the nucleopalladated intermediate, facilitating a protodepalladation event. This method affords highly functionalized γ-amino acids in good yields with high regioselectivity.

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Year:  2016        PMID： 27093112     DOI： 10.1021/jacs.6b02718

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN： 0002-7863            Impact factor:   15.419


  30 in total

1.  Synergistic palladium/enamine catalysis for asymmetric hydrocarbon functionalization of unactivated alkenes with ketones.

Authors:  Chiyu Wei; Xiaohan Ye; Qingyu Xing; Yong Hu; Yan Xie; Xiaodong Shi
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2.  Synthetic and Computational Studies on the Rhodium-Catalyzed Hydroamination of Aminoalkenes.

Authors:  Alexandra E Strom; David Balcells; John F Hartwig
Journal:  ACS Catal       Date:  2016-07-13       Impact factor: 13.084

3.  Transition-Metal-Catalyzed 1,2-Carboboration of Alkenes: Strategies, Mechanisms, and Stereocontrol.

Authors:  Zhen Liu; Yang Gao; Tian Zeng; Keary M Engle
Journal:  Isr J Chem       Date:  2019-09-10       Impact factor: 3.333

4.  Directed, Palladium(II)-Catalyzed Intermolecular Aminohydroxylation of Alkenes Using a Mild Oxidation System.

Authors:  Tian Zeng; Zhen Liu; Michael A Schmidt; Martin D Eastgate; Keary M Engle
Journal:  Org Lett       Date:  2018-06-11       Impact factor: 6.005

Review 5.  Palladium(0)-Catalyzed Directed syn-1,2-Carboboration and -Silylation: Alkene Scope, Applications in Dearomatization, and Stereocontrol by a Chiral Auxiliary.

Authors:  Zhen Liu; Jiahao Chen; Hou-Xiang Lu; Xiaohan Li; Yang Gao; John R Coombs; Matthew J Goldfogel; Keary M Engle
Journal:  Angew Chem Int Ed Engl       Date:  2019-10-08       Impact factor: 15.336

6.  Nickel-Catalyzed Reduction of Secondary and Tertiary Amides.

Authors:  Bryan J Simmons; Marie Hoffmann; Jaeyeon Hwang; Moritz K Jackl; Neil K Garg
Journal:  Org Lett       Date:  2017-03-24       Impact factor: 6.005

7.  Energy Decomposition Analyses Reveal the Origins of Catalyst and Nucleophile Effects on Regioselectivity in Nucleopalladation of Alkenes.

Authors:  Xiaotian Qi; Daniel G Kohler; Kami L Hull; Peng Liu
Journal:  J Am Chem Soc       Date:  2019-07-19       Impact factor: 15.419

8.  Direct Intermolecular Anti-Markovnikov Hydroazidation of Unactivated Olefins.

Authors:  Hongze Li; Shou-Jie Shen; Cheng-Liang Zhu; Hao Xu
Journal:  J Am Chem Soc       Date:  2019-05-30       Impact factor: 15.419

9.  Activation of diverse carbon-heteroatom and carbon-carbon bonds via palladium(II)-catalysed β-X elimination.

Authors:  Van T Tran; John A Gurak; Kin S Yang; Keary M Engle
Journal:  Nat Chem       Date:  2018-08-20       Impact factor: 24.427

10.  A practical method for N-alkylation of phosphinic (thio)amides with alcohols via transfer hydrogenation.

Authors:  Tanner C Jankins; Ziyang Qin; Keary M Engle
Journal:  Tetrahedron       Date:  2019-04-17       Impact factor: 2.457
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