Regioselective Copper-Catalyzed Boracarboxylation of Vinyl Arenes

被引：77

作者：

Butcher, Trevor W. ^{[1
]}

McClain, Edward J. ^{[1
]}

Hamilton, Tyler G. ^{[1
]}

Perrone, Trina M. ^{[1
]}

Kroner, Kayla M. ^{[1
]}

Donohoe, Gregory C. ^{[1
]}

Akhmedov, Novruz G. ^{[1
]}

Petersen, Jeffrey L. ^{[1
]}

Popp, Brian V. ^{[1
]}

机构：

[1] West Virginia Univ, C Eugene Bennett Dept Chem, Morgantown, WV 26505 USA

来源：

ORGANIC LETTERS | 2016年 / 18卷 / 24期

基金：

美国国家科学基金会;

关键词：

CARBON-DIOXIDE; MEDICINAL CHEMISTRY; TERMINAL ALKENES; CARBOXYLIC-ACIDS; BORYL COMPLEXES; CO2; ALKYNES; STYRENES; BORON; HYDROCARBOXYLATION;

D O I：

10.1021/acs.orglett.6b03326

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Regioselective copper-catalyzed boracarboxylation of vinyl arenes with bis(pinacolato)diboron and carbon dioxide has been achieved. New boron-functionalized alpha-aryl carboxylic acids, including nonsteroidal anti-inflammatory drugs (NSAIDs), are obtained in moderate to excellent yields. The synthetic utility of the transformation was shown through subsequent derivatization of the carbon-boron bond yielding formal hydroxy- and fluorocarboxylation products as well as anionic difluoroboralactones.

引用

页码：6428 / 6431

页数：4

共 59 条

[1] Catalysis for the Valorization of Exhaust Carbon: from CO2 to Chemicals, Materials, and Fuels. Technological Use of CO2 [J].

Aresta, Michele ;

Dibenedetto, Angela ;

Angelini, Antonella .

CHEMICAL REVIEWS, 2014, 114 (03) :1709-1742

[2] Therapeutic potential of boron-containing compounds [J].

Baker, Stephen J. ;

Ding, Charles Z. ;

Akama, Tsutomu ;

Zhang, Yong-Kang ;

Hernandez, Vincent ;

Xia, Yi .

FUTURE MEDICINAL CHEMISTRY, 2009, 1 (07) :1275-1288

[3] Olefin difunctionalizations via visible light photocatalysis [J].

Cao, Min-Yi ;

Ren, Xiang ;

Lu, Zhan .

TETRAHEDRON LETTERS, 2015, 56 (24) :3732-3742

[4] Transformation of Carbon Dioxide with Homogeneous Transition-Metal Catalysts: A Molecular Solution to a Global Challenge? [J].

Cokoja, Mirza ;

Bruckmeier, Christian ;

Rieger, Bernhard ;

Herrmann, Wolfgang A. ;

Kuehn, Fritz E. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (37) :8510-8537

[5] NHC-Cu-Catalyzed Enantioselective Hydroboration of Acyclic and Exocyclic 1,1-Disubstituted Aryl Alkenes [J].

Corberan, Rosa ;

Mszar, Nicholas W. ;

Hoveyda, Amir H. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (31) :7079-7082

[6] DFT studies of alkene insertions into Cu-B bonds in copper(I) boryl complexes [J].

Dang, Li ;

Zhao, Haitao ;

Lin, Zhenyang ;

Marder, Todd B. .

ORGANOMETALLICS, 2007, 26 (11) :2824-2832

[7] Fluorine in medicinal chemistry: a century of progress and a 60-year retrospective of selected highlights [J].

Filler, Robert ;

Saha, Rituparna .

FUTURE MEDICINAL CHEMISTRY, 2009, 1 (05) :777-791

[8] Copper-Catalyzed Silacarboxylation of Internal Alkynes by Employing Carbon Dioxide and Silylboranes [J].

Fujihara, Tetsuaki ;

Tani, Yosuke ;

Semba, Kazuhiko ;

Terao, Jun ;

Tsuji, Yasushi .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (46) :11487-11490

[9] Copper-Catalyzed Hydrocarboxylation of Alkynes Using Carbon Dioxide and Hydrosilanes [J].

Fujihara, Tetsuaki ;

Xu, Tinghua ;

Semba, Kazuhiko ;

Terao, Jun ;

Tsuji, Yasushi .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (02) :523-527

[10] Applications of Fluorine in Medicinal Chemistry [J].

Gillis, Eric P. ;

Eastman, Kyle J. ;

Hill, Matthew D. ;

Donnelly, David J. ;

Meanwell, Nicholas A. .

JOURNAL OF MEDICINAL CHEMISTRY, 2015, 58 (21) :8315-8359

← 1 2 3 4 5 6 →