Palladium-catalyzed, copper(I)-mediated coupling of boronic acids and benzylthiocyanate. A cyanide-free cyanation of boronic acids

被引:193
作者
Zhang, Zhihui [1 ]
Liebeskind, Lanny S. [1 ]
机构
[1] Emory Univ, Dept Chem, Atlanta, GA 30322 USA
关键词
D O I
10.1021/ol061741t
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A new method for the synthesis of nitriles is described. As a complement to the classic cyanation of aryl halides using cyanide sources and a transition metal catalyst, the palladium-catalyzed cross-coupling of thiocyanates with boronic acids in the presence of copper(I) thiophene-2-carboxylate (CuTC) affords nitriles in good to excellent yields.
引用
收藏
页码:4331 / 4333
页数:3
相关论文
共 36 条
[1]   Copper(I)-promoted palladium-catalyzed cross-coupling of unsaturated tri-n-butylstannane with heteroaromatic thioether [J].
Alphonse, FA ;
Suzenet, F ;
Keromnes, A ;
Lebret, B ;
Guillaumet, G .
ORGANIC LETTERS, 2003, 5 (06) :803-805
[2]  
Alphonse FA, 2002, SYNLETT, P447
[3]   Cooperative catalyst effects in palladium-mediated cyanation reactions of aryl halides and triflates [J].
Anderson, BA ;
Bell, EC ;
Ginah, FO ;
Harn, NK ;
Pagh, LM ;
Wepsiec, JP .
JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (23) :8224-8228
[4]  
CASSAR L, 1974, ADV CHEM SER, P252
[5]   A robust palladium-catalyzed cyanation procedure: beneficial effect of zinc acetate [J].
Chidambaram, R .
TETRAHEDRON LETTERS, 2004, 45 (07) :1441-1444
[6]   CYANATION OF AROMATIC HALIDES [J].
ELLIS, GP ;
ROMNEYALEXANDER, TM .
CHEMICAL REVIEWS, 1987, 87 (04) :779-794
[7]   DIMETHYLFORMAMIDE AS A USEFUL SOLVENT IN PREPARING NITRILES FROM ARYL HALIDES AND CUPROUS CYANIDE - IMPROVED ISOLATION TECHNIQUES [J].
FRIEDMAN, L ;
SHECHTER, H .
JOURNAL OF ORGANIC CHEMISTRY, 1961, 26 (07) :2522-&
[8]   Novel trans-spanned palladium complexes as efficient catalysts in mild and amine-free cyanation of aryl bromides under air [J].
Grossman, O ;
Gelman, D .
ORGANIC LETTERS, 2006, 8 (06) :1189-1191
[9]   A highly regioselective cyanothiolation of alkynes via oxidative addition of thiocyanates to tetrakis(triphenylphosphine)palladium(0) catalyst [J].
Kamiya, Ikuyo ;
Kawakami, Jun-ichi ;
Yano, Shigenobu ;
Nomoto, Akihiro ;
Ogawa, Akiya .
ORGANOMETALLICS, 2006, 25 (15) :3562-3564
[10]   Switchable catalysis: Modular synthesis of functionalized pyrimidinones via selective sulfide and halide cross-coupling chemistry [J].
Kusturin, C ;
Liebeskind, LS ;
Rahman, H ;
Sample, K ;
Schweitzer, B ;
Srogl, J ;
Neumann, WL .
ORGANIC LETTERS, 2003, 5 (23) :4349-4352