Pd-Catalyzed Regioselective Activation of gem-Difluorinated Cyclopropanes: A Highly Efficient Approach to 2-Fluorinated Allylic Scaffolds

被引：142

作者：

Xu, Jun ^{[1
,2
]}

Ahmed, Ebrahim-Alkhalil ^{[1
]}

Xiao, Bin ^{[1
]}

Lu, Qian-Qian ^{[1
]}

Wang, Yun-Long ^{[2
]}

Yu, Chu-Guo ^{[1
]}

Fu, Yao ^{[1
]}

机构：

[1] Univ Sci & Technol China, Dept Chem, CAS Key Lab Urban Pollutant Convers, IChEM, Hefei 230026, Peoples R China

[2] Hefei Univ Technol, Sch Med Engn, Hefei 230009, Peoples R China

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2015年 / 54卷 / 28期

关键词：

C(sp(3))F activation; CC bond cleavage; fluorinated compounds; gem-difluorinated cyclopropanes; palladium; F BOND ACTIVATION; C-F; SELECTIVE ACTIVATION; PEPTIDE ISOSTERES; BUILDING-BLOCKS; DIFLUOROCARBENE; FLUOROOLEFINS; INHIBITORS; HYDRODEFLUORINATION; FLUOROALKENES;

D O I：

10.1002/anie.201502308

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

An unprecedented Pd-catalyzed regioselective activation of gem-difluorinated cyclopropanes induced by CC bond cleavage is reported. It provides a general and efficient access to a variety of 2-fluoroallylic amines, ethers, esters, and alkylation products in high Z-selectivity, which are important skeletons in many biologically active molecules. In addition, the transformation represents the first general application of gem-difluorinated cyclopropanes as reaction partners in transition-metal-catalyzed cross-coupling reaction.

引用

页码：8231 / 8235

页数：5

共 85 条

[1] Synthesis and biological activity of fluorinated combretastatin analogues [J].

Alloatti, Domenico ;

Giannini, Giuseppe ;

Cabri, Walter ;

Lustrati, Isabella ;

Marzi, Mauro ;

Ciacci, Andrea ;

Gallo, Grazia ;

Tinti, M. Ornella ;

Marcellini, Marcella ;

Riccioni, Teresa ;

Guglielmi, Mario B. ;

Carminati, Paolo ;

Pisano, Claudio .

JOURNAL OF MEDICINAL CHEMISTRY, 2008, 51 (09) :2708-2721

[2] C-F Bond Activation in Organic Synthesis [J].

Amii, Hideki ;

Uneyama, Kenji .

CHEMICAL REVIEWS, 2009, 109 (05) :2119-2183

[3]

[Anonymous], 2013, ANGEW CHEM-GER EDIT, V125, P2146, DOI DOI 10.1002/ANGE.201209250

[4]

[Anonymous], 2013, ANGEW CHEM

[5]

[Anonymous], 2013, MODERN FLUOROORGANIC

[6]

[Anonymous], 2013, ANGEW CHEM

[7] Synthesis of poly(arylenevinylene)s with fluorinated vinylene units [J].

Babudri, Francesco ;

Cardone, Antonio ;

Farinola, Gianluca M. ;

Martinelli, Carmela ;

Mendichi, Raniero ;

Naso, Francesco ;

Striccoli, Marinella .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2008, 2008 (11) :1977-1982

[8] Fluorinated organic materials for electronic and optoelectronic applications: the role of the fluorine atom [J].

Babudri, Francesco ;

Farinola, Gianluca M. ;

Naso, Francesco ;

Ragni, Roberta .

CHEMICAL COMMUNICATIONS, 2007, (10) :1003-1022

[9] FLUOROALKENES AS PEPTIDE ISOSTERES - GROUND-STATE ANALOG INHIBITORS OF THERMOLYSIN [J].

BARTLETT, PA ;

OTAKE, A .

JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (10) :3107-3111

[10]

Bergeron M., 2011, ANGEW CHEM, V123, P11308

← 1 2 3 4 5 6 7 8 9 →