Literature DB >> 24383764

Asymmetric intermolecular Heck reaction of aryl halides.

Chunlin Wu1, Jianrong Steve Zhou.   

Abstract

The asymmetric intermolecular Heck reaction has been limited to aryl and vinyl triflates. Herein, we extend the reaction to aryl and vinyl bromides. Various cyclic olefins coupled with high enantioselectivity. Only bisphosphine oxides on a spiro backbone formed highly stereoselective Pd catalysts. The use of alcoholic solvents and alkylammonium salts were essential to promote halide dissociation from neutral arylpalladium complexes.

Entities:  

Year:  2014        PMID: 24383764     DOI: 10.1021/ja412277z

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


  12 in total

1.  Palladium-catalyzed regio- and stereoselective γ-arylation of tertiary allylic amines: identification of potent adenylyl cyclase inhibitors.

Authors:  Zhishi Ye; Tarsis F Brust; Val J Watts; Mingji Dai
Journal:  Org Lett       Date:  2015-02-10       Impact factor: 6.005

2.  Use of a new spirophosphine to achieve catalytic enantioselective [4 + 1] annulations of amines with allenes to generate dihydropyrroles.

Authors:  Søren Kramer; Gregory C Fu
Journal:  J Am Chem Soc       Date:  2015-03-17       Impact factor: 15.419

3.  Palladium-Catalyzed 1,3-Difunctionalization Using Terminal Alkenes with Alkenyl Nonaflates and Aryl Boronic Acids.

Authors:  Matthew S McCammant; Takashi Shigeta; Matthew S Sigman
Journal:  Org Lett       Date:  2016-03-28       Impact factor: 6.005

4.  Negishi Cross-Coupling Provides Alkylated Tryptophans and Tryptophan Regioisomers.

Authors:  Steffen Dachwitz; Bjarne Scharkowski; Norbert Sewald
Journal:  Chemistry       Date:  2021-11-11       Impact factor: 5.020

5.  A rational pre-catalyst design for bis-phosphine mono-oxide palladium catalyzed reactions.

Authors:  Yining Ji; Hongming Li; Alan M Hyde; Qinghao Chen; Kevin M Belyk; Katrina W Lexa; Jingjun Yin; Edward C Sherer; R Thomas Williamson; Andrew Brunskill; Sumei Ren; Louis-Charles Campeau; Ian W Davies; Rebecca T Ruck
Journal:  Chem Sci       Date:  2017-01-19       Impact factor: 9.825

6.  Access to enantioenriched 2,3- and 2,5-dihydrofurans with a fully substituted C2 stereocenter by Pd-catalyzed asymmetric intermolecular Heck reaction.

Authors:  Gustavo M Borrajo-Calleja; Vincent Bizet; Thomas Bürgi; Clément Mazet
Journal:  Chem Sci       Date:  2015-06-03       Impact factor: 9.825

7.  Quadruple C-H activation coupled to hydrofunctionalization and C-H silylation/borylation enabled by weakly coordinated palladium catalyst.

Authors:  Bo-Cheng Tang; Wen-Xuan Lin; Xiang-Long Chen; Cai He; Jin-Tian Ma; Yan-Dong Wu; Yu Lan; An-Xin Wu
Journal:  Nat Commun       Date:  2020-11-09       Impact factor: 14.919

8.  Introducing unactivated acyclic internal aliphatic olefins into a cobalt catalyzed allylic selective dehydrogenative Heck reaction.

Authors:  Soham Maity; Pravas Dolui; Rajesh Kancherla; Debabrata Maiti
Journal:  Chem Sci       Date:  2017-05-16       Impact factor: 9.825

9.  Molecular heterogeneous catalysts derived from bipyridine-based organosilica nanotubes for C-H bond activation.

Authors:  Shengbo Zhang; Hua Wang; Mei Li; Jinyu Han; Xiao Liu; Jinlong Gong
Journal:  Chem Sci       Date:  2017-04-19       Impact factor: 9.825

10.  Synthesis of 3-Substituted Pyrrolidines via Palladium-Catalyzed Hydroarylation.

Authors:  Joseph B Sweeney; Julien Doulcet; Bimod Thapa
Journal:  iScience       Date:  2018-11-01
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