Palladium-imidazolium carbene catalyzed aryl, vinyl, and alkyl Suzuki-Miyaura cross coupling

被引:153
作者
Andrus, MB [1 ]
Song, C [1 ]
机构
[1] Brigham Young Univ, Dept Chem & Biochem, Provo, UT 84602 USA
关键词
D O I
10.1021/ol016724c
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
[GRAPHICS] N,N-Bis-(2,6-diisopropylphenyl)dihydroimidazolium chloride with palladium(li) acetate (2 mol %) was used as catalyst, without added base, to efficiently cross couple aryl, vinyl, and alkyl boronates and boronic acids with aryldiazonium tetrafluoroborate substrates. The reactions were performed at 0 degreesC or rt, giving product in 2 to 4 h with 80 to 90% yields for isolated materials. Diazonium ions, formed in situ, also cross couple under these conditions.
引用
收藏
页码:3761 / 3764
页数:4
相关论文
共 24 条
[1]   Imidazolylidenes, imidazolinylidenes and imidazolidines [J].
Arduengo, AJ ;
Krafczyk, R ;
Schmutzler, R ;
Craig, HA ;
Goerlich, JR ;
Marshall, WJ ;
Unverzagt, M .
TETRAHEDRON, 1999, 55 (51) :14523-14534
[2]   Transannular macrocyclization via intramolecular B-alkyl Suzuki reaction [J].
Chemler, SR ;
Danishefsky, SJ .
ORGANIC LETTERS, 2000, 2 (17) :2695-2698
[3]   ALKYL NITRITE METAL HALIDE DEAMINATION REACTIONS .3. ARYLATION OF OLEFINIC COMPOUNDS IN DEAMINATION OF ARYLAMINES BY ALKYL NITRITES AND COPPER(II) HALIDES - CONVENIENT AND EFFECTIVE VARIATION OF MEERWEIN ARYLATION REACTION [J].
DOYLE, MP ;
SIEGFRIED, B ;
ELLIOTT, RC ;
DELLARIA, JF .
JOURNAL OF ORGANIC CHEMISTRY, 1977, 42 (14) :2431-2436
[4]  
Furstner A, 1998, SYNLETT, P161
[5]   Palladium/imidazolium salt catalyzed coupling of aryl halides with hypervalent organostannates [J].
Grasa, GA ;
Nolan, SP .
ORGANIC LETTERS, 2001, 3 (01) :119-122
[6]   Convenient and efficient Suzuki-Miyaura cross-coupling catalyzed by a palladium/diazabutadiene system [J].
Grasa, GA ;
Hillier, AC ;
Nolan, SP .
ORGANIC LETTERS, 2001, 3 (07) :1077-1080
[7]   Chiral oxazoline/imidazoline-2-ylidene complexes [J].
Herrmann, WA ;
Goossen, LJ ;
Spiegler, M .
ORGANOMETALLICS, 1998, 17 (11) :2162-2168
[8]   Chiral heterocyclic carbenes in asymmetric homogeneous catalysis [J].
Herrmann, WA ;
Goossen, LJ ;
Kocher, C ;
Artus, GRJ .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1996, 35 (23-24) :2805-2807
[9]   Efficient cross-coupling of aryl chlorides with aryl grignard reagents (Kumada reaction) mediated by a palladium/imidazolium chloride system [J].
Huang, JK ;
Nolan, SP .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (42) :9889-9890
[10]   Efficient cross-coupling reactions of aryl chlorides and bromides with phenyl- or vinyltrimethoxysilane mediated by a palladium/imidazolium chloride system [J].
Lee, HM ;
Nolan, SP .
ORGANIC LETTERS, 2000, 2 (14) :2053-2055