Literature DB >> 19209924

Efficient, regioselective palladium-catalyzed tandem Heck-isomerization reaction of aryl bromides and non-allylic benzyl alcohols.

Matthew L Crawley1, Kristin M Phipps, Igor Goljer, John F Mehlmann, Joseph T Lundquist, John W Ullrich, Cuijian Yang, Paige E Mahaney.   

Abstract

An efficient and mild method to couple aryl bromides and activated non-allylic alcohols in a Heck reaction with tandem isomerization to selectively afford high yields of 1,5-diarylalkan-1-ones has been developed. Mechanistic insight was gained through NMR studies of products derived from deuterium-labeled intermediates.

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Year:  2009        PMID: 19209924     DOI: 10.1021/ol900036y

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


  5 in total

1.  Alkenyl carbonyl derivatives in enantioselective redox relay Heck reactions: accessing α,β-unsaturated systems.

Authors:  Chun Zhang; Celine B Santiago; Lei Kou; Matthew S Sigman
Journal:  J Am Chem Soc       Date:  2015-06-04       Impact factor: 15.419

2.  Relative reactivity of alkenyl alcohols in the palladium-catalyzed redox-relay Heck reaction.

Authors:  Margaret J Hilton; Bin Cheng; Benjamin R Buckley; Liping Xu; Olaf Wiest; Matthew S Sigman
Journal:  Tetrahedron       Date:  2015-09-16       Impact factor: 2.457

3.  Enantioselective Dehydrogenative Heck Arylations of Trisubstituted Alkenes with Indoles to Construct Quaternary Stereocenters.

Authors:  Chun Zhang; Celine B Santiago; Jennifer M Crawford; Matthew S Sigman
Journal:  J Am Chem Soc       Date:  2015-12-10       Impact factor: 15.419

4.  Enantioselective redox-relay oxidative heck arylations of acyclic alkenyl alcohols using boronic acids.

Authors:  Tian-Sheng Mei; Erik W Werner; Alexander J Burckle; Matthew S Sigman
Journal:  J Am Chem Soc       Date:  2013-04-24       Impact factor: 15.419

5.  Palladium-Catalyzed Enantioselective Heck Alkenylation of Trisubstituted Allylic Alkenols: A Redox-Relay Strategy to Construct Vicinal Stereocenters.

Authors:  Chun Zhang; Brandon Tutkowski; Ryan J DeLuca; Leo A Joyce; Olaf Wiest; Matthew S Sigman
Journal:  Chem Sci       Date:  2016-12-09       Impact factor: 9.825

  5 in total

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