Palladium-catalyzed cross-coupling of B-benzyl-9-borabicyclo[3.3.1]nonane to furnish methylene-linked biaryls

被引:57
作者
Flaherty, A
Trunkfield, A
Barton, W
机构
[1] AstraZeneca R&D Charnwood, Loughborough LE11 5RH, Leics, England
[2] Univ Warwick, Dept Chem, Coventry CV4 7AL, W Midlands, England
关键词
D O I
10.1021/ol051929x
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
[GRAPHICS] Benzylboranes are noticeably uncommon partners within Suzuki-Miyaura coupling reactions. B-Benzyl-9-BBN was successfully coupled to a range of aryl/heteroaryl bromides, chlorides, and triflates to give pharmacologically important methylene-linked biaryl structures. Activated, deactivated, and sterically hindered substrates were successfully coupled in high yield using Pd(PPh3)(4) or Pd(OAc)(2) with SPhos as the catalyst system.
引用
收藏
页码:4975 / 4978
页数:4
相关论文
共 30 条
[1]  
[Anonymous], METAL CATALYSED CROS
[2]   Catalysts for Suzuki-Miyaura coupling processes: Scope and studies of the effect of ligand structure [J].
Barder, TE ;
Walker, SD ;
Martinelli, JR ;
Buchwald, SL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (13) :4685-4696
[3]   Palladium catalysts for the Suzuki cross-coupling reaction: An overview of recent advances [J].
Bellina, F ;
Carpita, A ;
Rossi, R .
SYNTHESIS-STUTTGART, 2004, (15) :2419-2440
[4]  
Chahen L, 2003, SYNLETT, P1668
[5]   Palladium catalyzed cross-coupling between phenyl- or naphthylboronic acids and benzylic bromides [J].
Chowdhury, S ;
Georghiou, PE .
TETRAHEDRON LETTERS, 1999, 40 (43) :7599-7603
[6]  
Furstner A, 1998, SYNLETT, P161
[7]   Synthesis of benzylic boronates via palladium-catalyzed cross-coupling reaction of bis(pinacolato)diboron with benzylic halides [J].
Giroux, A .
TETRAHEDRON LETTERS, 2003, 44 (02) :233-235
[8]   Aryl-aryl bond formation one century after the discovery of the Ullmann reaction [J].
Hassan, J ;
Sévignon, M ;
Gozzi, C ;
Schulz, E ;
Lemaire, M .
CHEMICAL REVIEWS, 2002, 102 (05) :1359-1469
[9]  
Heck R.F., 1985, PALLADIUM REAGENTS O
[10]   A general and straightforward route toward diarylmethanes. Integrated cross-coupling reactions using (2-Pyridyl)silylmethylstannane as an air-stable, storable, and versatile coupling platform [J].
Itami, K ;
Mineno, M ;
Kamei, T ;
Yoshida, J .
ORGANIC LETTERS, 2002, 4 (21) :3635-3638