Literature DB >> 28800242

Cobalt-Catalyzed Silylcarbonylation of Unactivated Secondary Alkyl Tosylates at Low Pressure.

Joan E Roque Peña1, Erik J Alexanian1.   

Abstract

A catalytic preparation of silyl enol ethers from unactivated secondary alkyl tosylates is reported. An inexpensive cobalt catalyst is used under mild conditions with low pressures of carbon monoxide. Nucleophilic, anionic cobalt carbonyls facilitate the catalytic activation of a range of alkyl tosylates. The silylcarbonylation offers a practical approach to synthetically valuable silyl enol ethers from simple starting materials.

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Year:  2017        PMID: 28800242      PMCID: PMC5623107          DOI: 10.1021/acs.orglett.7b02117

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


  11 in total

1.  Ni-catalyzed carboxylation of unactivated primary alkyl bromides and sulfonates with CO2.

Authors:  Yu Liu; Josep Cornella; Ruben Martin
Journal:  J Am Chem Soc       Date:  2014-07-31       Impact factor: 15.419

2.  Remote carboxylation of halogenated aliphatic hydrocarbons with carbon dioxide.

Authors:  Francisco Juliá-Hernández; Toni Moragas; Josep Cornella; Ruben Martin
Journal:  Nature       Date:  2017-05-03       Impact factor: 49.962

3.  Pd/light-accelerated atom-transfer carbonylation of alkyl iodides: applications in multicomponent coupling processes leading to functionalized carboxylic acid derivatives.

Authors:  Akira Fusano; Shuhei Sumino; Satoshi Nishitani; Takaya Inouye; Keisuke Morimoto; Takahide Fukuyama; Ilhyong Ryu
Journal:  Chemistry       Date:  2012-06-25       Impact factor: 5.236

Review 4.  The Mukaiyama aldol reaction: 40 years of continuous development.

Authors:  Jun-ichi Matsuo; Masahiro Murakami
Journal:  Angew Chem Int Ed Engl       Date:  2013-07-23       Impact factor: 15.336

5.  Carbonylation reactions of alkyl iodides through the interplay of carbon radicals and Pd catalysts.

Authors:  Shuhei Sumino; Akira Fusano; Takahide Fukuyama; Ilhyong Ryu
Journal:  Acc Chem Res       Date:  2014-04-08       Impact factor: 22.384

6.  Palladium-catalyzed carbonylative coupling reactions between Ar-X and carbon nucleophiles.

Authors:  Xiao-Feng Wu; Helfried Neumann; Matthias Beller
Journal:  Chem Soc Rev       Date:  2011-07-27       Impact factor: 54.564

7.  Palladium-Catalyzed Alkoxycarbonylation of Unactivated Secondary Alkyl Bromides at Low Pressure.

Authors:  Brendon T Sargent; Erik J Alexanian
Journal:  J Am Chem Soc       Date:  2016-06-10       Impact factor: 15.419

8.  Palladium-catalyzed carbonylation reactions of aryl halides and related compounds.

Authors:  Anne Brennführer; Helfried Neumann; Matthias Beller
Journal:  Angew Chem Int Ed Engl       Date:  2009       Impact factor: 15.336

9.  Coupling reaction of alkyl chlorides with silyl enolates catalyzed by indium trihalide.

Authors:  Yoshihiro Nishimoto; Makoto Yasuda; Akio Baba
Journal:  Org Lett       Date:  2007-11-02       Impact factor: 6.005

10.  Mechanistic studies on alpha-trifluoromethylation of ketones via silyl enol ethers and its application to other carbonyl compounds.

Authors:  Kazuyuki Sato; Takashi Yuki; Ryoji Yamaguchi; Tetsuya Hamano; Atsushi Tarui; Masaaki Omote; Itsumaro Kumadaki; Akira Ando
Journal:  J Org Chem       Date:  2009-05-15       Impact factor: 4.354

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  1 in total

1.  Halogenation Reactions of Alkyl Alcohols Employing Methyl Grignard Reagents.

Authors:  Nadia Hirbawi; Patricia C Lin; Elizabeth R Jarvo
Journal:  J Org Chem       Date:  2022-09-01       Impact factor: 4.198

  1 in total

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