Literature DB >> 27218134

Catalytic, Enantioselective Addition of Alkyl Radicals to Alkenes via Visible-Light-Activated Photoredox Catalysis with a Chiral Rhodium Complex.

Haohua Huo1, Klaus Harms1, Eric Meggers1,2.   

Abstract

An efficient enantioselective addition of alkyl radicals, oxidatively generated from organotrifluoroborates, to acceptor-substituted alkenes is catalyzed by a bis-cyclometalated rhodium catalyst (4 mol %) under photoredox conditions. The practical method provides yields up to 97% with excellent enantioselectivities up to 99% ee and can be classified as a redox neutral, electron-transfer-catalyzed reaction.

Entities:  

Year:  2016        PMID: 27218134     DOI: 10.1021/jacs.6b03399

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


  29 in total

1.  1,2-Boron Shifts of β-Boryl Radicals Generated from Bis-boronic Esters Using Photoredox Catalysis.

Authors:  Daniel Kaiser; Adam Noble; Valerio Fasano; Varinder K Aggarwal
Journal:  J Am Chem Soc       Date:  2019-09-03       Impact factor: 15.419

2.  Visible-light excitation of iminium ions enables the enantioselective catalytic β-alkylation of enals.

Authors:  Mattia Silvi; Charlie Verrier; Yannick P Rey; Luca Buzzetti; Paolo Melchiorre
Journal:  Nat Chem       Date:  2017-03-20       Impact factor: 24.427

3.  Preparation of chiral-at-metal catalysts and their use in asymmetric photoredox chemistry.

Authors:  Jiajia Ma; Xiao Zhang; Xiaoqiang Huang; Shipeng Luo; Eric Meggers
Journal:  Nat Protoc       Date:  2018-03-01       Impact factor: 13.491

4.  Rhodium-Catalyzed Enantioselective Radical Addition of CX4 Reagents to Olefins.

Authors:  Bo Chen; Cheng Fang; Peng Liu; Joseph M Ready
Journal:  Angew Chem Int Ed Engl       Date:  2017-06-14       Impact factor: 15.336

5.  Reductive Arylation of Arylidene Malonates Using Photoredox Catalysis.

Authors:  Rick C Betori; Karl A Scheidt
Journal:  ACS Catal       Date:  2019-10-17       Impact factor: 13.700

6.  Photoenzymatic Generation of Unstabilized Alkyl Radicals: An Asymmetric Reductive Cyclization.

Authors:  Phillip D Clayman; Todd K Hyster
Journal:  J Am Chem Soc       Date:  2020-09-03       Impact factor: 15.419

Review 7.  Photoredox-Catalyzed C-H Functionalization Reactions.

Authors:  Natalie Holmberg-Douglas; David A Nicewicz
Journal:  Chem Rev       Date:  2021-09-29       Impact factor: 60.622

Review 8.  Recent Advances in Photoredox-Mediated Radical Conjugate Addition Reactions: An Expanding Toolkit for the Giese Reaction.

Authors:  Anastasia L Gant Kanegusuku; Jennifer L Roizen
Journal:  Angew Chem Int Ed Engl       Date:  2021-07-21       Impact factor: 16.823

9.  Photoredox Catalysis in Organic Chemistry.

Authors:  Megan H Shaw; Jack Twilton; David W C MacMillan
Journal:  J Org Chem       Date:  2016-08-01       Impact factor: 4.354

Review 10.  Radicals: Reactive Intermediates with Translational Potential.

Authors:  Ming Yan; Julian C Lo; Jacob T Edwards; Phil S Baran
Journal:  J Am Chem Soc       Date:  2016-09-26       Impact factor: 15.419

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