Palladium-Catalyzed Cross-Coupling of Benzyl Thioacetates and Aryl Halides

被引：32
|
作者：
Wager, Krista M. [1 ]
Daniels, Matthew H. [1 ]
机构：
[1] Merck Res Labs, Dept Chem, Boston, MA 02115 USA
来源：
ORGANIC LETTERS | 2011年 / 13卷 / 15期
关键词：
ONE-POT SYNTHESIS; S BOND FORMATION; DIORGANYL SELENIDES; OXIDATIVE ADDITION; C-N; EFFICIENT; THIOLS; SULFUR; SULFIDES; BROMIDES;
D O I：
10.1021/ol201564j
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A method for preparing benzyl aryl thioethers utilizing an in situ deprotection of benzyl thioacetates as an alternative to free thiols as starting materials has been developed and optimized. Good to excellent yields of diverse benzyl aryl thioethers are obtained with air-stable, odor-free, and easy to prepare thioesters. A one-pot protocol for forming benzyl aryl thioethers from a benzyl halide, potassium thioacetate, and an aryl bromide has also been demonstrated.
引用
收藏
页码：4052 / 4055
页数：4
相关论文
共 50 条
  • [1] Palladium-catalyzed cross-coupling of benzyl thioacetates and aryl halides
    Wager, Krista M.
    Daniels, Matthew
    [J]. ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2012, 243
  • [2] Palladium-Catalyzed Cross-Coupling of Aryl Thioacetates and Chloro(hetero)arenes
    Zhao, Tan
    Liang, Feng
    Cai, Mingjun
    Chen, Junling
    Kang, Chuanqing
    Wang, Hongda
    Wu, Qiang
    [J]. ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2020, 9 (02) : 214 - 217
  • [3] PALLADIUM-CATALYZED CROSS-COUPLING OF VINYLALANES WITH ARYL HALIDES
    ALHASSAN, MI
    [J]. SYNTHETIC COMMUNICATIONS, 1987, 17 (12) : 1413 - 1420
  • [4] Palladium-catalyzed cross-coupling of aryl halides with acylsilanes
    Schmink, Jason R.
    Krska, Shane W.
    Tudge, Matthew T.
    [J]. ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2011, 242
  • [5] Palladium-catalyzed cross-coupling reaction of alkyltrifluorosilanes with aryl halides
    Matsuhashi, H
    Asai, S
    Hirabayashi, K
    Mori, A
    Hiyama, T
    [J]. BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1997, 70 (02) : 437 - 444
  • [6] Palladium-catalyzed cross-coupling reaction of potassium diaryldifluoroborates with aryl halides
    Ito, T
    Iwai, T
    Mizuno, T
    Ishino, Y
    [J]. SYNLETT, 2003, (10) : 1435 - 1438
  • [7] Palladium-Catalyzed Cross-Coupling of Aryl Halides Using Organotitanium Nucleophiles
    Lee, Hang Wai
    Lam, Fuk Loi
    So, Chau Ming
    Lau, Chak Po
    Chan, Albert S. C.
    Kwong, Fuk Yee
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (40) : 7436 - 7439
  • [8] Minimizing the Amount of Nitromethane in Palladium-Catalyzed Cross-Coupling with Aryl Halides
    Walvoord, Ryan R.
    Kozlowski, Marisa C.
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2013, 78 (17): : 8859 - 8864
  • [9] PALLADIUM-CATALYZED CROSS-COUPLING REACTION OF FUNCTIONALIZED ALKYLTRIFLUOROSILANES WITH ARYL HALIDES
    MATSUHASHI, H
    KUROBOSHI, M
    HATANAKA, Y
    HIYAMA, T
    [J]. TETRAHEDRON LETTERS, 1994, 35 (35) : 6507 - 6510
  • [10] Palladium-catalyzed cross-coupling reaction of triarylbismuths with aryl halides and triflates
    Rao, MLN
    Yamazaki, O
    Shimada, S
    Tanaka, T
    Suzuki, Y
    Tanaka, M
    [J]. ORGANIC LETTERS, 2001, 3 (25) : 4103 - 4105
12345