Rhodium-catalyzed interconversion between acid fluorides and thioesters controlled using heteroatom acceptors

被引：34
作者：
Arisawa, Mieko [1 ]
Yamada, Toru [1 ]
Yamaguchi, Masahiko [1 ,2 ]
机构：
[1] Tohoku Univ, Grad Sch Pharmaceut Sci, Dept Organ Chem, Sendai, Miyagi 9808578, Japan
[2] Tohoku Univ, Adv Inst Mat Res, WPI Res Ctr, Sendai, Miyagi 9808577, Japan
来源：
TETRAHEDRON LETTERS | 2010年 / 51卷 / 47期
关键词：
EXCHANGE-REACTION; ORGANOSULFUR COMPOUNDS; DISULFIDES; ESTERS;
D O I：
10.1016/j.tetlet.2010.09.009
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A rhodium complex catalyzed the equilibrium acyl transfer reaction between acid fluorides and thioesters. In the presence of fluoride or thiolate acceptors, the reaction could be shifted to either product. RhH(PPh3)(4)-dppe catalyzed the reaction of acid fluorides and diorgano disulfides in the presence of triphenylphosphine giving thioesters, which was accompanied by triphenylphosphine difluoride. The same complex catalyzed the reaction of aryl thioesters and hexafluorobenzene giving acid fluorides, which was accompanied by 1,4-di(arylthio)-2,3,5,6-tetrafluorobenzenes. (C) 2010 Published by Elsevier Ltd.
引用
收藏
页码：6090 / 6092
页数：3
相关论文
共 19 条
  • [1] AREVALO MJ, 2009, EUR J ORG CHEM, V617, P625
  • [2] Equilibrating C-S bond formation by C-H and S-S bond metathesis. Rhodium-catalyzed alkylthiolation reaction of 1-alkynes with disulfides
    Arisawa, M
    Fujimoto, K
    Morinaka, S
    Yamaguchi, M
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (35) : 12226 - 12227
  • [3] Rhodium-catalyzed substitution reaction of aryl fluorides with disulfides:: p-orientation in the polyarylthiolation of polyfluorobenzenes
    Arisawa, Mieko
    Suzuki, Takaaki
    Ishikawa, Tomofumi
    Yamaguchi, Masahiko
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (37) : 12214 - +
  • [4] Rhodium-catalyzed alkylthio exchange reaction of thioester and disulfide
    Arisawa, Mieko
    Kubota, Tomohiro
    Yamaguchi, Masahiko
    [J]. TETRAHEDRON LETTERS, 2008, 49 (12) : 1975 - 1978
  • [5] Transition-metal-catalyzed synthesis of organosulfur compounds
    Arisawa, Mieko
    Yamaguchi, Masahiko
    [J]. PURE AND APPLIED CHEMISTRY, 2008, 80 (05) : 993 - 1003
  • [6] Transition-metal-catalyzed synthesis of organophosphorous and organosulfur compounds
    Arisawa, Mieko
    Yamaguchi, Masahiko
    [J]. JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN, 2007, 65 (12) : 1213 - 1224
  • [7] Synthesis of acylphosphine sulfides by rhodium-catalyzed reaction of acid fluorides and diphosphine disulfides
    Arisawa, Mieko
    Yamada, Toru
    Yamaguchi, Masahiko
    [J]. TETRAHEDRON LETTERS, 2010, 51 (38) : 4957 - 4958
  • [8] Rhodium-Catalyzed Organothio Exchange Reaction of α-Organothioketones with Disulfides
    Arisawa, Mieko
    Toriyama, Fumihiko
    Yamaguchi, Masahiko
    [J]. CHEMICAL & PHARMACEUTICAL BULLETIN, 2010, 58 (10) : 1349 - 1352
  • [9] RhCl3-CATALYZED DISULFIDE EXCHANGE REACTION OF INSULIN AND DITHIODIGLYCOLIC ACID
    Arisawa, Mieko
    Kuwajima, Manabu
    Suwa, Atsushi
    Yamaguchi, Masahiko
    [J]. HETEROCYCLES, 2010, 80 (02) : 1239 - 1248
  • [10] Aminodifluorosulfinium Tetrafluoroborate Salts as Stable and Crystalline Deoxofluorinating Reagents
    Beaulieu, Francis
    Beauregard, Louis-Philippe
    Courchesne, Gabriel
    Couturier, Michel
    LaFlamme, Francois
    L'Heureux, Alexandre
    [J]. ORGANIC LETTERS, 2009, 11 (21) : 5050 - 5053
12