Silver-Catalyzed Decarboxylative Alkynylation of α,α-Difluoroarylacetic Acids with Ethynylbenziodoxolone Reagents

被引：72

作者：

Chen, Fei ^{[1
]}

Hashmi, A. Stephen K. ^{[1
,2
]}

机构：

[1] Heidelberg Univ, Inst Organ Chem, Neuenheimer Feld 270, D-69120 Heidelberg, Germany

[2] King Abdulaziz Univ, Fac Sci, Dept Chem, Jeddah 21589, Saudi Arabia

来源：

ORGANIC LETTERS | 2016年 / 18卷 / 12期

关键词：

ARYL BORONIC ACIDS; ALIPHATIC CARBOXYLIC-ACIDS; ALPHA-ARYLATION; ALKENES; ALKYNES; TRIFLUOROMETHYLATION; ACCESS; DIFLUOROALKYLATION; FLUOROALKYLATION; ORGANOBORONS;

D O I：

10.1021/acs.orglett.6b01188

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A decarboxylating alkynylation of alpha,alpha-difluoroarylacetic acids with ethynylbenziodoxolone reagents is reported. AgNO3 serves as the catalyst and K2S2O8 as the oxidant. A series of functional groups were tolerated, and moderate to good yields were obtained.

引用

页码：2880 / 2882

页数：3

共 56 条

[1] Transition-metal-catalyzed addition of heteroatom-hydrogen bonds to alkynes [J].

Alonso, F ;

Beletskaya, IP ;

Yus, M .

CHEMICAL REVIEWS, 2004, 104 (06) :3079-3159

[2] Synthesis of new difluoroalkyl propargylic ketones and their use for the preparation of fluorinated heterocycles [J].

Bannwarth, Pierre ;

Gree, Danielle ;

Gree, Rene .

TETRAHEDRON LETTERS, 2010, 51 (18) :2413-2415

[3] Copper-free click chemistry for dynamic in vivo imaging [J].

Baskin, Jeremy M. ;

Prescher, Jennifer A. ;

Laughlin, Scott T. ;

Agard, Nicholas J. ;

Chang, Pamela V. ;

Miller, Isaac A. ;

Lo, Anderson ;

Codelli, Julian A. ;

Bertozzi, Carolyn R. .

PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 2007, 104 (43) :16793-16797

[4] Access to Difluoromethylated Alkynes through the Castro-Stephens Reaction [J].

Besset, Tatiana ;

Poisson, Thomas ;

Pannecoucke, Xavier .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2014, 2014 (32) :7220-7225

[5] Direct Alkynylation of Indole and Pyrrole Heterocycles [J].

Brand, Jonathan P. ;

Charpentier, Julie ;

Waser, Jerome .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (49) :9346-9349

[6] One-Pot, Three-Component Arylalkynyl Sulfone Synthesis [J].

Chen, C. Chun ;

Waser, Jerome .

ORGANIC LETTERS, 2015, 17 (03) :736-739

[7] Room temperature alkynylation of H-phosphi(na)tes and secondary phosphine oxides with ethynylbenziodoxolone (EBX) reagents [J].

Chen, C. Chun ;

Waser, Jerome .

CHEMICAL COMMUNICATIONS, 2014, 50 (85) :12923-12926

[8] The sonogashira reaction:: A booming methodology in synthetic organic chemistry [J].

Chinchilla, Rafael ;

Najera, Carmen .

CHEMICAL REVIEWS, 2007, 107 (03) :874-922

[9] Copper-Mediated Oxidative Trifluoromethylation of Boronic Acids [J].

Chu, Lingling ;

Qing, Feng-Ling .

ORGANIC LETTERS, 2010, 12 (21) :5060-5063

[10] Silver-Catalyzed Decarboxylative Allylation of Aliphatic Carboxylic Acids in Aqueous Solution [J].

Cui, Lei ;

Chen, He ;

Liu, Chao ;

Li, Chaozhong .

ORGANIC LETTERS, 2016, 18 (09) :2188-2191

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