Copper-mediated cross-coupling of aryl boronic acids and alkyl thiols

被引:307
作者
Herradura, PS
Pendola, KA
Guy, RK
机构
[1] Univ Calif San Francisco, Dept Pharmaceut Chem, San Francisco, CA 94143 USA
[2] Univ Calif San Francisco, Dept Mol & Cellular Pharmacol, San Francisco, CA 94143 USA
关键词
D O I
10.1021/ol005832g
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
GRAPHICS The cross-coupling of aryl boronic acids and alkanethiols mediated by copper(II) acetate and pyridine in anhydrous dimethylformamide affords aryl alkyl sulfides in good yield with a wide variety of substituted aryl boronic acids. The method is applicable to the synthesis of aryl sulfides of cysteine.
引用
收藏
页码:2019 / 2022
页数:4
相关论文
共 16 条
[1]   Convenient synthesis of aromatic thiols from phenols [J].
Arnould, JC ;
Didelot, M ;
Cadilhac, C ;
Pasquet, MJ .
TETRAHEDRON LETTERS, 1996, 37 (26) :4523-4524
[2]   ASYMMETRIC-SYNTHESIS OF BETA-SUBSTITUTED ALPHA-AMINO-ACIDS VIA A CHIRAL NI-II COMPLEX OF DEHYDROALANINE [J].
BELOKON, YN ;
SAGYAN, AS ;
DJAMGARYAN, SM ;
BAKHMUTOV, VI ;
BELIKOV, VM .
TETRAHEDRON, 1988, 44 (17) :5507-5514
[3]   New N- and O-arylations with phenylboronic acids and cupric acetate [J].
Chan, DMT ;
Monaco, KL ;
Wang, RP ;
Winters, MP .
TETRAHEDRON LETTERS, 1998, 39 (19) :2933-2936
[4]   A NEW, PALLADIUM-CATALYZED SYNTHESIS OF AROMATIC MERCAPTURIC ACID-DERIVATIVES [J].
CIATTINI, PG ;
MORERA, E ;
ORTAR, G .
TETRAHEDRON LETTERS, 1995, 36 (23) :4133-4136
[5]   Cupric acetate mediated N-arylation by arylboronic acids: A preliminary investigation into the scope of application [J].
Cundy, DJ ;
Forsyth, SA .
TETRAHEDRON LETTERS, 1998, 39 (43) :7979-7982
[6]   S-ARYL-L-CYSTEINE S,S-DIOXIDES - DESIGN, SYNTHESIS, AND EVALUATION OF A NEW CLASS OF INHIBITORS OF KYNURENINASE [J].
DUA, RK ;
TAYLOR, EW ;
PHILLIPS, RS .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (04) :1264-1270
[7]   Synthesis of diaryl ethers through the copper-promoted arylation of phenols with arylboronic acids. An expedient synthesis of thyroxine [J].
Evans, DA ;
Katz, JL ;
West, TR .
TETRAHEDRON LETTERS, 1998, 39 (19) :2937-2940
[8]   SYNTHESIS OF AROMATIC S-SUBSTITUTED DERIVATIVES OF N-ACETYL-L-CYSTEINE [J].
HICKMAN, RJS ;
CHRISTIE, BJ ;
GUY, RW ;
WHITE, TJ .
AUSTRALIAN JOURNAL OF CHEMISTRY, 1985, 38 (06) :899-904
[9]   A practical synthesis of nelfinavir, an HIV-protease inhibitor, using a novel chiral C4 building block:: (5R,6S)-2,2-dimethyl-5-hydroxy-1,3-dioxepan-6-ylammonium acetate [J].
Inaba, T ;
Birchler, AG ;
Yamada, Y ;
Sagawa, S ;
Yokota, K ;
Ando, K ;
Uchida, I .
JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (22) :7582-7583
[10]   Viracept (nelfinavir mesylate, AG1343): A potent, orally bioavailable inhibitor of HIV-1 protease [J].
Kaldor, SW ;
Kalish, VJ ;
Davies, JF ;
Shetty, BV ;
Fritz, JE ;
Appelt, K ;
Burgess, JA ;
Campanale, KM ;
Chirgadze, NY ;
Clawson, DK ;
Dressman, BA ;
Hatch, SD ;
Khalil, DA ;
Kosa, MB ;
Lubbehusen, PP ;
Muesing, MA ;
Patick, AK ;
Reich, SH ;
Su, KS ;
Tatlock, JH .
JOURNAL OF MEDICINAL CHEMISTRY, 1997, 40 (24) :3979-3985