Literature DB >> 28691820

Oxidative [1,2]-Brook Rearrangements Exploiting Single-Electron Transfer: Photoredox-Catalyzed Alkylations and Arylations.

Yifan Deng1, Qi Liu1, Amos B Smith1.   

Abstract

Oxidative [1,2]-Brook rearrangements via hypervalent silicon intermediates induced by photoredox-catalyzed single-electron transfer have been achieved, permitting the formation of reactive radical species that can engage in alkylations and arylations.

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Year:  2017        PMID： 28691820      PMCID： PMC5575796          DOI： 10.1021/jacs.7b05165

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


  16 in total

1.  Dual catalysis sees the light: combining photoredox with organo-, acid, and transition-metal catalysis.

Authors:  Matthew N Hopkinson; Basudev Sahoo; Jun-Long Li; Frank Glorius
Journal:  Chemistry       Date:  2014-03-05       Impact factor: 5.236

2.  Organic Photoredox Catalysis.

Authors:  Nathan A Romero; David A Nicewicz
Journal:  Chem Rev       Date:  2016-06-10       Impact factor: 60.622

3.  Synthetic Applications of Proton-Coupled Electron Transfer.

Authors:  Emily C Gentry; Robert R Knowles
Journal:  Acc Chem Res       Date:  2016-07-29       Impact factor: 22.384

4.  On the radical brook rearrangement. Reactivity of alpha-silyl alcohols, alpha-silyl alcohol nitrite esters, and beta-haloacylsilanes under radical-forming conditions

Authors: 
Journal:  J Org Chem       Date:  2000-04-21       Impact factor: 4.354

5.  Reactions of a N-acyliminium ion pool with benzylsilanes. Implication of a radical/cation/radical cation chain mechanism involving oxidative C-Si bond cleavage.

Authors:  Tomokazu Maruyama; Yusuke Mizuno; Ikuo Shimizu; Seiji Suga; Jun-Ichi Yoshida
Journal:  J Am Chem Soc       Date:  2007-01-30       Impact factor: 15.419

6.  Evolution of dithiane-based strategies for the construction of architecturally complex natural products.

Authors:  Amos B Smith; Christopher M Adams
Journal:  Acc Chem Res       Date:  2004-06       Impact factor: 22.384

7.  Silicates as Latent Alkyl Radical Precursors: Visible-Light Photocatalytic Oxidation of Hypervalent Bis-Catecholato Silicon Compounds.

Authors:  Vincent Corcé; Lise-Marie Chamoreau; Etienne Derat; Jean-Philippe Goddard; Cyril Ollivier; Louis Fensterbank
Journal:  Angew Chem Int Ed Engl       Date:  2015-07-24       Impact factor: 15.336

8.  The direct arylation of allylic sp(3) C-H bonds via organic and photoredox catalysis.

Authors:  James D Cuthbertson; David W C MacMillan
Journal:  Nature       Date:  2015-03-05       Impact factor: 49.962

9.  Activation of C-H bonds via the merger of photoredox and organocatalysis: a coupling of benzylic ethers with Schiff bases.

Authors:  Dominik Hager; David W C MacMillan
Journal:  J Am Chem Soc       Date:  2014-12-02       Impact factor: 15.419

Review 10.  Dual Catalysis Strategies in Photochemical Synthesis.

Authors:  Kazimer L Skubi; Travis R Blum; Tehshik P Yoon
Journal:  Chem Rev       Date:  2016-04-25       Impact factor: 60.622
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  6 in total

1.  Design, Synthesis, and Application of Polymer-Supported Silicon-Transfer Agents for Cross-Coupling Reactions with Organolithium Reagents.

Authors:  Minh H Nguyen; Kevin T O'Brien; Amos B Smith
Journal:  J Org Chem       Date:  2017-10-02       Impact factor: 4.354

2.  Photoredox-catalyzed branch-selective pyridylation of alkenes for the expedient synthesis of Triprolidine.

Authors:  Shengqing Zhu; Jian Qin; Fang Wang; Huan Li; Lingling Chu
Journal:  Nat Commun       Date:  2019-02-14       Impact factor: 14.919

3.  Tuning the reactivity of alkoxyl radicals from 1,5-hydrogen atom transfer to 1,2-silyl transfer.

Authors:  Zhaoliang Yang; Yunhong Niu; Xiaoqian He; Suo Chen; Shanshan Liu; Zhengyu Li; Xiang Chen; Yunxiao Zhang; Yu Lan; Xiao Shen
Journal:  Nat Commun       Date:  2021-04-09       Impact factor: 14.919

4.  Cascade cyclization of alkene-tethered acylsilanes and allylic sulfones enabled by unproductive energy transfer photocatalysis.

Authors:  Yunxiao Zhang; Yizhi Zhang; Chen Ye; Xiaotian Qi; Li-Zhu Wu; Xiao Shen
Journal:  Nat Commun       Date:  2022-10-16       Impact factor: 17.694

5.  Lewis Basic Salt-Promoted Organosilane Coupling Reactions with Aromatic Electrophiles.

Authors:  Tyler W Reidl; Jeffrey S Bandar
Journal:  J Am Chem Soc       Date:  2021-07-27       Impact factor: 16.383

6.  Direct transfer of tri- and di-fluoroethanol units enabled by radical activation of organosilicon reagents.

Authors:  Xiang Chen; Xingxing Gong; Zhengyu Li; Gang Zhou; Zhihong Zhu; Weilu Zhang; Shanshan Liu; Xiao Shen
Journal:  Nat Commun       Date:  2020-06-02       Impact factor: 14.919
  6 in total

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