gem-Selective Cross-Dimerization and Cross-Trimerization of Alkynes with Silylacetylenes Promoted by a Rhodium-Pyridine-N-Heterocyclic Carbene Catalyst

被引：29

作者：

Azpiroz, Ramon ^{[1
]}

Rubio-Perez, Laura ^{[1
]}

Castarlenas, Ricardo ^{[1
]}

Perez-Torrente, Jesus J. ^{[1
]}

Oro, Luis A. ^{[1
]}

机构：

[1] Univ Zaragoza, CSIC, Dept Quim Inorgan, Fac Ciencias,ISQCH, E-50009 Zaragoza, Spain

来源：

CHEMCATCHEM | 2014年 / 6卷 / 09期

关键词：

CC coupling; dimerization; trimerization; carbenes; rhodium; C-H ACTIVATION; TERMINAL ALKYNES; INTERNAL ALKYNES; COMPLEXES; PALLADIUM; TRIISOPROPYLSILYLACETYLENE; ADDITIONS; STRATEGY; IRIDIUM; ACCESS;

D O I：

10.1002/cctc.201402327

中图分类号：

O64 [物理化学（理论化学）、化学物理学];

学科分类号：

070304 ; 081704 ;

摘要：

The gem-selective cross-dimerization and -trimerization of silylacetylenes with alkynes through CH activation using a rhodium(I)-pyridine-N-heterocyclic carbene catalyst have been developed. This reaction is applied to various aliphatic or aromatic terminal alkynes, internal alkynes, and gem-1,3-disubsituted enynes to afford the corresponding enynes and dienynes with high regio- and stereoselectivities and in good isolated yields (up to 91%).

引用

页码：2587 / 2592

页数：6

共 59 条

[1] REGIOSELECTIVE HOMOMERIZATION AND CODIMERIZATION OF 1-ALKYNES LEADING TO 2,4-DISUBSTITUTED 1-BUTEN-3-YNES BY CATALYSIS OF A (ETA-5-C5ME5)2TICL2/RMGX SYSTEM [J].

AKITA, M ;

YASUDA, H ;

NAKAMURA, A .

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1984, 57 (02) :480-487

[2] A New Access to 4H-Quinolizines from 2-Vinylpyridine and Alkynes Promoted by Rhodium-N-Heterocyclic-Carbene Catalysts [J].

Azpiroz, Ramon ;

Di Giuseppe, Andrea ;

Castarlenas, Ricardo ;

Perez-Torrente, Jesus J. ;

Oro, Luis A. .

CHEMISTRY-A EUROPEAN JOURNAL, 2013, 19 (12) :3812-3816

[3] SELECTIVE, ZIRCONIUM-MEDIATED CROSS-COUPLING OF ALKYNES - SYNTHESIS OF ISOMERICALLY PURE 1,3-DIENES AND 1,4-DIIODO 1,3-DIENES [J].

BUCHWALD, SL ;

NIELSEN, RB .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (08) :2870-2874

[4]

Bustelo E., 2005, DIXNEUF HDB C H TRAN, V1

[5] Facile and selective copper-palladium catalyzed addition of terminal alkynes to activated alkynes in water [J].

Chen, L ;

Li, CJ .

TETRAHEDRON LETTERS, 2004, 45 (13) :2771-2774

[6] Chemo- and regioselective dimerization of terminal alkynes promoted by methylaluminoxane [J].

Dash, AK ;

Eisen, MS .

ORGANIC LETTERS, 2000, 2 (06) :737-740

[7] Total synthesis of (+)-brasilenyne. Application of an intramolecular silicon-assisted cross-coupling reaction [J].

Denmark, SE ;

Yang, SM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (39) :12432-12440

[8] Ligand-Controlled Regioselectivity in the Hydrothiolation of Alkynes by Rhodium N-Heterocyclic Carbene Catalysts [J].

Di Giuseppe, Andrea ;

Castarlenas, Ricardo ;

Perez-Torrente, Jesus J. ;

Crucianelli, Marcello ;

Polo, Victor ;

Sancho, Rodrigo ;

Lahoz, Fernando J. ;

Oro, Luis A. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (19) :8171-8183

[9] Marine natural products [J].

Faulkner, DJ .

NATURAL PRODUCT REPORTS, 2001, 18 (01) :1-49

[10] Photoactive Chromium(III)-Cyclam Complexes with Axially Bound geminal-Diethynylethenes [J].

Forrest, William P. ;

Cao, Zhi ;

Hambrick, H. Rhodes ;

Prentice, Boone M. ;

Fanwick, Phillip E. ;

Wagenknecht, Paul S. ;

Ren, Tong .

EUROPEAN JOURNAL OF INORGANIC CHEMISTRY, 2012, (34) :5616-5620

← 1 2 3 4 5 6 →