Cross-coupling of cyclopropyl- and cyclobutyltrifluoroborates with aryl and heteroaryl chlorides

被引：88

作者：

Molander, Gary A. ^{[1
]}

Gormisky, Paul E. ^{[1
]}

机构：

[1] Univ Penn, Dept Chem, Roy & Diana Vagelos Labs, Philadelphia, PA 19104 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2008年 / 73卷 / 19期

关键词：

D O I：

10.1021/jo801269m

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] Suitable conditions were found for the Suzuki-Miyaura cross-coupling reaction of potassium cyclopropyl and cyclobutyltrifluoroborates with aryl chlorides. Both of these secondary alkyl trifluoroborates coupled in moderate to excellent yield with electron-rich, electron-poor, and hindered aryl chlorides to give a variety of substituted aryl cyclopropanes and cyclobutanes.

引用

页码：7481 / 7485

页数：5

共 35 条

[1] Catalysts for Suzuki-Miyaura coupling processes: Scope and studies of the effect of ligand structure [J].

Barder, TE ;

Walker, SD ;

Martinelli, JR ;

Buchwald, SL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (13) :4685-4696

[2] Bis(pyrimidine)-based palladium catalysts: synthesis, X-ray structure and applications in Heck-, Suzuki-, Sonogashira-Hagihara couplings and amination reactions [J].

Buchmeiser, MR ;

Schareina, T ;

Kempe, R ;

Wurst, K .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2001, 634 (01) :39-46

[3] Diastereoselective synthesis of 1,2,3-substituted potassium cyclopropyl trifluoroborates via an unusual zinc-boron exchange [J].

Charette, AB ;

Mathieu, S ;

Fournier, JF .

SYNLETT, 2005, (11) :1779-1782

[4]

Chemler SR, 2001, ANGEW CHEM INT EDIT, V40, P4544, DOI 10.1002/1521-3773(20011217)40:24<4544::AID-ANIE4544>3.0.CO

[5]

2-N

[6] Palladium-catalyzed alkylation of sp2 and sp3 C-H bonds with methylboroxine and alkylboronic acids:: Two distinct C-H activation pathways [J].

Chen, Xiao ;

Goodhue, Charles E. ;

Yu, Jin-Quan .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (39) :12634-12635

[7] Potassium organotrifluoroborates: New perspectives in organic synthesis [J].

Darses, Sylvain ;

Genet, Jean-Pierre .

CHEMICAL REVIEWS, 2008, 108 (01) :288-325

[8] Efficient cross-coupling of secondary alkyltrifluoroborates with aryl chlorides-reaction discovery using parallel microscale experimentation [J].

Dreher, Spencer D. ;

Dormer, Peter G. ;

Sandrock, Deidre L. ;

Molander, Gary A. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (29) :9257-+

[9] Palladium-catalyzed cross-coupling of stereospecific potassium cyclopropyl trifluoroborates with aryl bromides [J].

Fang, GH ;

Yan, ZJ ;

Deng, MZ .

ORGANIC LETTERS, 2004, 6 (03) :357-360

[10]

Fürstner A, 2001, SYNLETT, P290

← 1 2 3 4 →