Literature DB >> 23734764

Copper-catalyzed oxidative Heck reactions between alkyltrifluoroborates and vinyl arenes.

Timothy W Liwosz1, Sherry R Chemler.   

Abstract

We report herein that potassium alkyltrifluoroborates can be utilized in oxidative Heck-type reactions with vinyl arenes. The reaction is catalyzed by a Cu(OTf)2/1,10-phenanthroline with MnO2 as the stoichiometric oxidant. In addition to the alkyl Heck, amination, esterification, and dimerization reactions of alkyltrifluoroborates are demonstrated under analogous reaction conditions. Evidence for an alkyl radical intermediate is presented.

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Year:  2013        PMID： 23734764      PMCID： PMC3978782          DOI： 10.1021/ol401220b

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


  46 in total

1.  Rhodium-catalyzed coupling reactions of arylboronic acids to olefins in aqueous media.

Authors:  M Lautens; A Roy; K Fukuoka; K Fagnou; B Martín-Matute
Journal:  J Am Chem Soc       Date:  2001-06-06       Impact factor: 15.419

2.  Oxidation of alkyl trifluoroborates: an opportunity for tin-free radical chemistry.

Authors:  Geoffroy Sorin; Rocio Martinez Mallorquin; Yohan Contie; Alexandre Baralle; Max Malacria; Jean-Philippe Goddard; Louis Fensterbank
Journal:  Angew Chem Int Ed Engl       Date:  2010-11-08       Impact factor: 15.336

Review 3.  Potassium organotrifluoroborates: new perspectives in organic synthesis.

Authors:  Sylvain Darses; Jean-Pierre Genet
Journal:  Chem Rev       Date:  2007-12-21       Impact factor: 60.622

4.  Oxidation of catecholboron enolates with TEMPO.

Authors:  Martin Pouliot; Philippe Renaud; Kurt Schenk; Armido Studer; Thomas Vogler
Journal:  Angew Chem Int Ed Engl       Date:  2009       Impact factor: 15.336

5.  A ruthenium-catalyzed reaction of aromatic ketones with arylboronates: a new method for the arylation of aromatic compounds via C-H bond cleavage.

Authors:  Fumitoshi Kakiuchi; Shintaro Kan; Kimitaka Igi; Naoto Chatani; Shinji Murai
Journal:  J Am Chem Soc       Date:  2003-02-19       Impact factor: 15.419

6.  Selective formation of secondary amides via the copper-catalyzed cross-coupling of alkylboronic acids with primary amides.

Authors:  Steven A Rossi; Kirk W Shimkin; Qun Xu; Luis M Mori-Quiroz; Donald A Watson
Journal:  Org Lett       Date:  2013-04-23       Impact factor: 6.005

7.  Synthesis and minisci reactions of organotrifluoroborato building blocks.

Authors:  Marc Presset; Nicolas Fleury-Brégeot; Daniel Oehlrich; Frederik Rombouts; Gary A Molander
Journal:  J Org Chem       Date:  2013-04-17       Impact factor: 4.354

8.  Direct cross-coupling reaction of simple alkenes with acrylates catalyzed by palladium catalyst.

Authors:  Yun-He Xu; Jun Lu; Teck-Peng Loh
Journal:  J Am Chem Soc       Date:  2009-02-04       Impact factor: 15.419

9.  Cobalt dinitrosoalkane complexes in the C-H functionalization of olefins.

Authors:  Jennifer M Schomaker; W Christopher Boyd; Ian C Stewart; F Dean Toste; Robert G Bergman
Journal:  J Am Chem Soc       Date:  2008-03-05       Impact factor: 15.419

10.  Base-free Mizoroki-Heck reaction catalyzed by rhodium complexes.

Authors:  Rémi Martinez; Florina Voica; Jean-Pierre Genet; Sylvain Darses
Journal:  Org Lett       Date:  2007-07-18       Impact factor: 6.005
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  12 in total

1.  Synthesis of 2-Aryl- and 2-Vinylpyrrolidines via Copper-Catalyzed Coupling of Styrenes and Dienes with Potassium β-Aminoethyl Trifluoroborates.

Authors:  Chanchamnan Um; Sherry R Chemler
Journal:  Org Lett       Date:  2016-05-10       Impact factor: 6.005

2.  Allylic functionalization of unactivated olefins with Grignard reagents.

Authors:  Hongli Bao; Liela Bayeh; Uttam K Tambar
Journal:  Angew Chem Int Ed Engl       Date:  2014-01-23       Impact factor: 15.336

3.  Copper-Catalyzed Amidation of Primary and Secondary Alkyl Boronic Esters.

Authors:  Luis M Mori-Quiroz; Kirk W Shimkin; Sina Rezazadeh; Ryan A Kozlowski; Donald A Watson
Journal:  Chemistry       Date:  2016-09-22       Impact factor: 5.236

4.  Stereoselective and Regioselective Synthesis of Heterocycles via Copper-Catalyzed Additions of Amine Derivatives and Alcohols to Alkenes.

Authors:  Sherry R Chemler; Shuklendu D Karyakarte; Zainab M Khoder
Journal:  J Org Chem       Date:  2017-09-29       Impact factor: 4.354

5.  Synthesis of Benzylureas and Related Amine Derivatives via Copper-Catalyzed Three-Component Carboamination of Styrenes.

Authors:  Jonathan J Kennedy-Ellis; Erik D Boldt; Sherry R Chemler
Journal:  Org Lett       Date:  2020-10-19       Impact factor: 6.005

6.  Enantioselective copper-catalyzed carboetherification of unactivated alkenes.

Authors:  Michael T Bovino; Timothy W Liwosz; Nicole E Kendel; Yan Miller; Nina Tyminska; Eva Zurek; Sherry R Chemler
Journal:  Angew Chem Int Ed Engl       Date:  2014-05-05       Impact factor: 15.336

7.  Vinylation of Benzylic Amines via C-N Bond Functionalization of Benzylic Pyridinium Salts.

Authors:  Weiye Guan; Jennie Liao; Mary P Watson
Journal:  Synthesis (Stuttg)       Date:  2018-06-08       Impact factor: 3.157

8.  Contrasteric coupling of allenes and tetrahydroisoquinolines by iron-catalysed allenic C(sp2)-H functionalisation.

Authors:  Yue Xia; Nicholas W Wade; Philip N Palermo; Yidong Wang; Yi-Ming Wang
Journal:  Chem Commun (Camb)       Date:  2021-12-09       Impact factor: 6.222

9.  Copper-Catalyzed Synthesis of N-Aryl and N-Sulfonyl Indoles from 2-Vinylanilines with O2 as Terminal Oxidant and TEMPO as Co-Catalyst.

Authors:  Timothy W Liwosz; Sherry R Chemler
Journal:  Synlett       Date:  2014       Impact factor: 2.454

10.  Transition-Metal-Catalyzed Alkyl Heck-Type Reactions.

Authors:  Daria Kurandina; Padon Chuentragool; Vladimir Gevorgyan
Journal:  Synthesis (Stuttg)       Date:  2019-02-07       Impact factor: 3.157
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