Rhodium catalysed chemo- and stereoselective arylative and alkenylative cyclisation reactions of unsymmetric diynes containing a terminal alkyne moiety with organoboronic acids

被引:15
作者
Artok, Levent [1 ]
Kus, Melih [1 ]
Urer, Bagdagul N. [1 ]
Turkmen, Gulsah [1 ]
Aksin-Artok, Ozge [2 ]
机构
[1] Izmir Inst Technol, Dept Chem, Fac Sci, TR-35430 Izmir, Turkey
[2] Dortmund Univ Technol, D-44227 Dortmund, Germany
关键词
ARYLBORONIC ACIDS; CYCLOADDITION REACTIONS; RING EXPANSION; COMPLEXES; LIGANDS; ORGANORHODIUM(I); POLYMERIZATION; 1,4-ADDITION; ACETYLENES; 1,6-DIYNES;
D O I
10.1039/b926553h
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Unsymmetric diynes possessing a terminal alkyne moiety reacted with organoboronic acids both chemo- and stereoselectively to afford arylated or alkenylated exocyclic dienes by catalysis from the [Rh(cod)OCH(3)](2) complex. The use of a polar protic solvent, e.g. CH(3)OH is required for the success of the process under mild conditions.
引用
收藏
页码:2060 / 2067
页数:8
相关论文
共 39 条
[1]  
Adams R, 1925, ORG SYNTH, V4, P11
[2]   ACETYLENES .1. MIXED DIHALIDES AND HALOHYDRINS FROM BUTYNEDIOL [J].
BAILEY, WJ ;
FUJIWARA, E .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1955, 77 (01) :165-166
[3]   RETRACTED: Rhodium-catalyzed arylative and alkenylative cyclization of 1,5-enynes induced by geminal carbometalation of alkynes (Retracted Article) [J].
Chen, Yiyun ;
Lee, Chulbom .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (49) :15598-15599
[4]   Rhodium-catalyzed reaction of terminal alkynes with allylamine leading to (E)-3-alkylidene N-heterocycles [J].
Fukumoto, Yoshiya ;
Kinashi, Fuyuko ;
Kawahara, Takuya ;
Chatani, Naoto .
ORGANIC LETTERS, 2006, 8 (20) :4641-4643
[5]  
Giordano G., 1979, Inorg. Synth, V19, P218, DOI DOI 10.1002/9780470132500.CH50
[6]   Catalytic cycle of rhodium-catalyzed asymmetric 1,4-addition of organoboronic acids.: Arylrhodium, oxa-π-allylrhodium, and hydroxorhodium intermediates [J].
Hayashi, T ;
Takahashi, M ;
Takaya, Y ;
Ogasawara, M .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (18) :5052-5058
[7]   Rhodium-catalyzed hydroarylation of alkynes with arylboronic acids: 1,4-shift of rhodium from 2-aryl-1-alkenylrhodium to 2-alkenylarylrhodium intermediate [J].
Hayashi, T ;
Inoue, K ;
Taniguchi, N ;
Ogasawara, M .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (40) :9918-9919
[8]   Rhodium-catalyzed 1,4-addition of arylboronic acids to α,β-unsaturated carbonyl compounds:: Large accelerating effects of bases and ligands [J].
Itooka, R ;
Iguchi, Y ;
Miyaura, N .
JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (15) :6000-6004
[9]   Rhodium-catalyzed reductive cyclization of 1,6-diynes and 1,6-enynes mediated by hydrogen: Catalytic C-C bond formation via capture of hydrogenation intermediates [J].
Jang, HY ;
Krische, MJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (25) :7875-7880
[10]   RHODIUM ALKOXIDE COMPLEXES - FORMATION OF AN UNUSUALLY STRONG INTERMOLECULAR HYDROGEN-BOND IN (PME3)3RH-OTOL(HOTOL) [J].
KEGLEY, SE ;
SCHAVERIEN, CJ ;
FREUDENBERGER, JH ;
BERGMAN, RG ;
NOLAN, SP ;
HOFF, CD .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (21) :6563-6565