Cobalt-Catalyzed Arylzincation of Alkynes

被引:53
作者
Murakami, Kei [1 ]
Yorimitsu, Hideki [1 ]
Oshima, Koichiro [1 ]
机构
[1] Kyoto Univ, Dept Chem Mat, Grad Sch Engn, Nishikyo Ku, Kyoto 6158510, Japan
关键词
CARBON BOND-FORMATION; STEREOSELECTIVE-SYNTHESIS; TETRASUBSTITUTED ALKENES; SYNTHETIC REACTIONS; SELECTIVE SYNTHESIS; COUPLING REACTIONS; REAGENTS; CARBOZINCATION; EFFICIENT; ARYLMAGNESIATION;
D O I
10.1021/ol900883j
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Cobalt(II) bromide catalyzes arylzincation of alkynes with arylzinc iodide center dot lithium chloride complexes in acetonitrile. The scope of the arylzincation is wide enough to use unfunctionalized alkynes, such as 6-dodecyne, as well as arylacetylenes. The inherent functional group compatibility of arylzinc reagents allows preparation of various functionalized styrene derivatives. The reaction is applicable to the efficient and stereoselective synthesis of a synthetic estrogen and its derivative.
引用
收藏
页码:2373 / 2375
页数:3
相关论文
共 31 条
[11]   Cobalt(II)-Catalyzed Regio- and Stereoselective Hydroarylation of Alkynes with Organoboronic Acids [J].
Lin, Pao-Shun ;
Jeganmohan, Masilamani ;
Cheng, Chien-Hong .
CHEMISTRY-A EUROPEAN JOURNAL, 2008, 14 (36) :11296-11299
[12]   Geometrically selective synthesis of functionalized β,β-disubstituted vinylic sulfoxides by Cu-catalyzed conjugate addition of organozinc reagents to 1-alkynyl sulfoxides [J].
Maezaki, N ;
Sawamoto, H ;
Yoshigami, R ;
Suzuki, T ;
Tanaka, T .
ORGANIC LETTERS, 2003, 5 (08) :1345-1347
[13]  
Marek I, 1998, METAL-CATALYZED CROSS-COUPLING REACTIONS, P271
[14]   Chromium-catalyzed arylmagnesiation of alkynes [J].
Murakami, Kei ;
Ohmiya, Hirohisa ;
Yorimitsu, Hideki ;
Oshima, Koichiro .
ORGANIC LETTERS, 2007, 9 (08) :1569-1571
[16]   Recent Advances in Efficient and Selective Synthesis of Di-, Tri-, and Tetrasubstituted Alkenes via Pd-Catalyzed Alkenylation-Carbonyl Olefination Synergy [J].
Negishi, Ei-Ichi ;
Huang, Zhihong ;
Wang, Guangwei ;
Mohan, Swathi ;
Wang, Chao .
ACCOUNTS OF CHEMICAL RESEARCH, 2008, 41 (11) :1474-1485
[17]   Highly selective synthetic reactions by the combined use of organometallic reagents and radical species [J].
Oshima, Koichiro .
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 2008, 81 (01) :1-24
[18]   Secondary Alkyl Halides in Transition-Metal-Catalyzed Cross-Coupling Reactions [J].
Rudolph, Alena ;
Lautens, Mark .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (15) :2656-2670
[19]  
Shinokubo H, 2004, EUR J ORG CHEM, V2004, P2081
[20]   Rhodium-catalyzed addition of arylzinc reagents to aryl alkynyl ketones:: Synthesis of β,β-disubstituted indanones [J].
Shintani, R ;
Hayashi, T .
ORGANIC LETTERS, 2005, 7 (10) :2071-2073