Literature DB >> 31390217

Regioselective Single-Electron Tsuji-Trost Reaction of Allylic Alcohols: A Photoredox/Nickel Dual Catalytic Approach.

Zheng-Jun Wang1,2, Shuai Zheng1, Eugénie Romero1, Jennifer K Matsui1, Gary A Molander1.   

Abstract

A radical-mediated functionalization of allyl alcohol derived partners with a variety of alkyl 1,4-dihydropyridines via photoredox/nickel dual catalysis is described. This transformation transpires with high linear and E-selectivity, avoiding the requirement of harsh conditions (e.g., strong base, elevated temperature). Additionally, using aryl sulfinate salts as radical precursors, allyl sulfones can also be obtained. Kinetic isotope effect experiments implicated oxidative addition of the nickel catalyst to the allylic electrophile as the turnover-limiting step, supporting previous computational studies.

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Year:  2019        PMID: 31390217      PMCID: PMC7091330          DOI: 10.1021/acs.orglett.9b02473

Source DB:  PubMed          Journal:  Org Lett        ISSN: 1523-7052            Impact factor:   6.005


  36 in total

1.  Allylic Amination.

Authors:  Mogens Johannsen; Karl Anker Jørgensen
Journal:  Chem Rev       Date:  1998-06-18       Impact factor: 60.622

2.  TBAI-catalyzed selective synthesis of sulfonamides and β-aryl sulfonyl enamines: coupling of arenesulfonyl chlorides and sodium sulfinates with tert-amines.

Authors:  Hongmei Jiang; Xiaoyue Tang; Zhihui Xu; Huixian Wang; Kang Han; Xiaolan Yang; Yuanyuan Zhou; Yong-Lai Feng; Xian-Yong Yu; Qingwen Gui
Journal:  Org Biomol Chem       Date:  2019-03-06       Impact factor: 3.876

3.  Nickel-Catalyzed Reductive Allylation of Tertiary Alkyl Halides with Allylic Carbonates.

Authors:  Haifeng Chen; Xiao Jia; Yingying Yu; Qun Qian; Hegui Gong
Journal:  Angew Chem Int Ed Engl       Date:  2017-09-12       Impact factor: 15.336

4.  Studies on the mechanism of allylic coupling reactions: a hammett analysis of the coupling of aryl silicate derivatives.

Authors:  Krupa H Shukla; Philip DeShong
Journal:  J Org Chem       Date:  2008-07-11       Impact factor: 4.354

Review 5.  Recent advances in homogeneous nickel catalysis.

Authors:  Sarah Z Tasker; Eric A Standley; Timothy F Jamison
Journal:  Nature       Date:  2014-05-15       Impact factor: 49.962

6.  Nickel-catalyzed asymmetric negishi cross-couplings of secondary allylic chlorides with alkylzincs.

Authors:  Sunghee Son; Gregory C Fu
Journal:  J Am Chem Soc       Date:  2008-02-08       Impact factor: 15.419

7.  Decarboxylative allylation of amino alkanoic acids and esters via dual catalysis.

Authors:  Simon B Lang; Kathryn M O'Nele; Jon A Tunge
Journal:  J Am Chem Soc       Date:  2014-09-22       Impact factor: 15.419

8.  Base-Free Photoredox/Nickel Dual-Catalytic Cross-Coupling of Ammonium Alkylsilicates.

Authors:  Matthieu Jouffroy; David N Primer; Gary A Molander
Journal:  J Am Chem Soc       Date:  2015-12-24       Impact factor: 15.419

9.  Cross-Coupling of Sodium Sulfinates with Aryl, Heteroaryl, and Vinyl Halides by Nickel/Photoredox Dual Catalysis.

Authors:  Huifeng Yue; Chen Zhu; Magnus Rueping
Journal:  Angew Chem Int Ed Engl       Date:  2018-01-05       Impact factor: 15.336

10.  Desulfonative photoredox alkylation of N-heteroaryl sulfones - an acid-free approach for substituted heteroarene synthesis.

Authors:  Zheng-Jun Wang; Shuai Zheng; Jennifer K Matsui; Zhipeng Lu; Gary A Molander
Journal:  Chem Sci       Date:  2019-03-14       Impact factor: 9.825

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  2 in total

1.  Nickel-Catalyzed Removal of Alkene Protecting Group of Phenols, Alcohols via Chain Walking Process.

Authors:  Chenkai Meng; Haolin Niu; Juehan Ning; Wengang Wu; Jun Yi
Journal:  Molecules       Date:  2020-01-30       Impact factor: 4.411

2.  A photoredox catalysed Heck reaction via hole transfer from a Ru(ii)-bis(terpyridine) complex to graphene oxide.

Authors:  Marta Rosenthal; Jörg K N Lindner; Uwe Gerstmann; Armin Meier; W Gero Schmidt; René Wilhelm
Journal:  RSC Adv       Date:  2020-11-25       Impact factor: 4.036

  2 in total

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