Literature DB >> 27080165

Reductive Cross-Coupling of Conjugated Arylalkenes and Aryl Bromides with Hydrosilanes by Cooperative Palladium/Copper Catalysis.

Kazuhiko Semba1, Kenta Ariyama2, Hong Zheng3, Ryohei Kameyama2, Shigeyoshi Sakaki4, Yoshiaki Nakao5.   

Abstract

A method for the reductive cross-coupling of conjugated arylalkenes and aryl bromides with hydrosilanes by cooperative palladium/copper catalysis was developed, thus resulting in the highly regioselective formation of various 1,1-diarylalkanes, including a biologically active molecule. Under the applied reaction conditions, high levels of functional-group tolerance were observed, and the reductive cross-coupling of internal alkynes with aryl bromides afforded trisubstituted alkenes.
© 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  alkenes; alkynes; copper; cross-coupling; palladium

Year:  2016        PMID: 27080165     DOI: 10.1002/anie.201511975

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN: 1433-7851            Impact factor:   15.336


  16 in total

1.  Practical Intermolecular Hydroarylation of Terminal Alkenes via Reductive Heck Coupling.

Authors:  John A Gurak; Keary M Engle
Journal:  ACS Catal       Date:  2018-08-24       Impact factor: 13.084

2.  Differential Dihydrofunctionalization of Terminal Alkynes: Synthesis of Benzylic Alkyl Boronates through Reductive Three-Component Coupling.

Authors:  Megan K Armstrong; Gojko Lalic
Journal:  J Am Chem Soc       Date:  2019-04-03       Impact factor: 15.419

3.  Catalytic Enantioselective Arylboration of Alkenylarenes.

Authors:  Kaitlyn M Logan; M Kevin Brown
Journal:  Angew Chem Int Ed Engl       Date:  2016-12-21       Impact factor: 15.336

4.  CuH-Catalyzed Olefin Functionalization: From Hydroamination to Carbonyl Addition.

Authors:  Richard Y Liu; Stephen L Buchwald
Journal:  Acc Chem Res       Date:  2020-05-13       Impact factor: 22.384

5.  Enantioselective Olefin Hydrocyanation without Cyanide.

Authors:  Alexander W Schuppe; Gustavo M Borrajo-Calleja; Stephen L Buchwald
Journal:  J Am Chem Soc       Date:  2019-11-18       Impact factor: 15.419

6.  Enantioselective Preparation of Arenes with β-Stereogenic Centers: Confronting the 1,1-Disubstituted Olefin Problem Using CuH/Pd Cooperative Catalysis.

Authors:  Zhaohong Lu; Stephen L Buchwald
Journal:  Angew Chem Int Ed Engl       Date:  2020-06-30       Impact factor: 15.336

7.  A Dual Palladium and Copper Hydride Catalyzed Approach for Alkyl-Aryl Cross-Coupling of Aryl Halides and Olefins.

Authors:  Stig D Friis; Michael T Pirnot; Lauren N Dupuis; Stephen L Buchwald
Journal:  Angew Chem Int Ed Engl       Date:  2017-05-16       Impact factor: 15.336

8.  Stereospecific Synthesis of E-Alkenes through Anti-Markovnikov Hydroalkylation of Terminal Alkynes.

Authors:  Avijit Hazra; Jason Chen; Gojko Lalic
Journal:  J Am Chem Soc       Date:  2019-08-02       Impact factor: 15.419

9.  Synthesis of 1,1'-Diarylethanes and Related Systems by Displacement of Trichloroacetimidates with Trimethylaluminum.

Authors:  Nivedita S Mahajani; John D Chisholm
Journal:  J Org Chem       Date:  2018-03-08       Impact factor: 4.354

10.  Enantioselective Hydroalkenylation of Olefins with Enol Sulfonates Enabled by Dual Copper Hydride and Palladium Catalysis.

Authors:  Alexander W Schuppe; James Levi Knippel; Gustavo M Borrajo-Calleja; Stephen L Buchwald
Journal:  J Am Chem Soc       Date:  2021-03-30       Impact factor: 15.419

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