Tailored Cobalt‐Catalysts for Reductive Alkylation of Anilines with Carboxylic Acids under Mild Conditions

We have developed I2/KH2PO2 and KI/P(OEt)3 strategy syntheses of esters from carboxylic acids and alcohols through different reaction mechanisms. The advantages of present protocol: mild conditions and late-stage diversification of natural products.

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ChemInform Abstract: A FACILE CONVERSION OF CARBOXYLIC ACIDS TO CARBINOLS UNDER MILD CONDITIONS

Chemischer Informationsdienst ◽

10.1002/chin.197415170 ◽

1974 ◽

Vol 5 (15) ◽

pp. no-no

Author(s):

P. L. HALL ◽

R. B. PERFETTI

Keyword(s):

Carboxylic Acids ◽

Mild Conditions

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ChemInform Abstract: Nucleophilic Acyl Substitution via Aromatic Cation Activation of Carboxylic Acids: Rapid Generation of Acid Chlorides under Mild Conditions.

ChemInform ◽

10.1002/chin.201032057 ◽

2010 ◽

Vol 41 (32) ◽

pp. no-no

Author(s):

David J. Hardee ◽

Lyudmila Kovalchuke ◽

Tristan H. Lambert

Keyword(s):

Carboxylic Acids ◽

Acid Chlorides ◽

Mild Conditions ◽

Cation Activation ◽

Rapid Generation ◽

Nucleophilic Acyl Substitution

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Selective Synthesis of 1-O-Alkyl(poly)glycerol Ethers by Catalytic Reductive Alkylation of Carboxylic Acids with a Recyclable Catalytic System

ChemSusChem ◽

10.1002/cssc.201200447 ◽

2012 ◽

Vol 5 (12) ◽

pp. 2397-2409 ◽

Cited By ~ 30

Author(s):

Marc Sutter ◽

Wissam Dayoub ◽

Estelle Métay ◽

Yann Raoul ◽

Marc Lemaire

Keyword(s):

Carboxylic Acids ◽

Catalytic System ◽

Selective Synthesis ◽

Reductive Alkylation ◽

Glycerol Ethers

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Convenient Preparation of Primary Amides via Activation of Carboxylic Acids with Ethyl Chloroformate and Triethylamine under Mild Conditions

Chemistry Letters ◽

10.1246/cl.130096 ◽

2013 ◽

Vol 42 (6) ◽

pp. 580-582 ◽

Cited By ~ 9

Author(s):

Takuya Noguchi ◽

Masahiro Sekine ◽

Yuki Yokoo ◽

Seunghee Jung ◽

Nobuyuki Imai

Keyword(s):

Carboxylic Acids ◽

Ethyl Chloroformate ◽

Mild Conditions ◽

Convenient Preparation

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Ni/Co-Catalyzed Homo-Coupling of Alkyl Tosylates

Molecules ◽

10.3390/molecules24081458 ◽

2019 ◽

Vol 24 (8) ◽

pp. 1458 ◽

Cited By ~ 5

Author(s):

Kimihiro Komeyama ◽

Ryusuke Tsunemitsu ◽

Takuya Michiyuki ◽

Hiroto Yoshida ◽

Itaru Osaka

Keyword(s):

Electron Transfer ◽

Oxidative Addition ◽

Alkyl Halides ◽

Cobalt Catalysts ◽

Single Electron ◽

Single Electron Transfer ◽

Mild Conditions

A direct reductive homo-coupling of alkyl tosylates has been developed by employing a combination of nickel and nucleophilic cobalt catalysts. A single-electron-transfer-type oxidative addition is a pivotal process in the well-established nickel-catalyzed coupling of alkyl halides. However, the method cannot be applied to the homo-coupling of ubiquitous alkyl tosylates due to the high-lying σ*(C–O) orbital of the tosylates. This paper describes a Ni/Co-catalyzed protocol for the activation of alkyl tosylates on the construction of alkyl dimers under mild conditions.

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Decarboxylative sulfenylation of amino acids via metallaphotoredox catalysis

Organic Chemistry Frontiers ◽

10.1039/c9qo00817a ◽

2019 ◽

Vol 6 (18) ◽

pp. 3224-3227 ◽

Cited By ~ 11

Author(s):

Lidan Wei ◽

Chengjuan Wu ◽

Chen-Ho Tung ◽

Wenguang Wang ◽

Zhenghu Xu

Keyword(s):

Amino Acids ◽

Visible Light ◽

Carboxylic Acids ◽

Mild Conditions ◽

Cooperative Catalysis

A nickel/visible light photoredox co-catalyzed decarboxylative thiolation reaction of carboxylic acids has been developed. This odorless sulfenylation reaction proceeded well via a nickel/photoredox cooperative catalysis pathway under very mild conditions.

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