Organic synthesis in water: Green protocol for the conjugate addition of thiols to p-quinones

被引:42
|
作者
Yadav, J. S. [1 ]
Swamy, T. [1 ]
Reddy, B. V. Subba [1 ]
Rao, D. Kishna [1 ]
机构
[1] Indian Inst Chem Technol, Div Organ Chem, Hyderabad 500007, Andhra Pradesh, India
关键词
thia-Michael addition; quinones; diaryl sulfides; aryl alkyl sulfides;
D O I
10.1016/j.molcata.2007.04.037
中图分类号
O64 [物理化学(理论化学)、化学物理学];
学科分类号
070304 ; 081704 ;
摘要
The Michael addition of thiols to p-quinones proceeds efficiently in water at room temperature without a catalyst. Significant rate acceleration of this reaction is observed in water compared to organic solvents. Water played a dual role in simultaneously activating the quinones and thiols. This new methodology constitutes an easy, highly efficient and green synthesis of diaryl sulfides and aryl alkyl sulfides. (c) 2007 Elsevier B.V. All rights reserved.
引用
收藏
页码:116 / 119
页数:4
相关论文
共 50 条
  • [1] Green protocol for conjugate addition of amines to p-quinones accelerated by water
    Jhillu S. Yadav
    Basi V. Subba Reddy
    Tallapally Swamy
    Kattela Shiva Shankar
    Monatshefte für Chemie - Chemical Monthly, 2008, 139 : 1317 - 1320
  • [2] Green protocol for conjugate addition of amines to p-quinones accelerated by water
    Yadav, Jhillu S.
    Reddy, Basi V. Subba
    Swamy, Tallapally
    Shankar, Kattela Shiva
    MONATSHEFTE FUR CHEMIE, 2008, 139 (11): : 1317 - 1320
  • [3] Bi(OTf)3-catalyzed a facile conjugate addition of indoles to p-quinones:: synthesis of 3-indolyl quinones
    Yadav, JS
    Reddy, BVS
    Swamy, T
    TETRAHEDRON LETTERS, 2003, 44 (51) : 9121 - 9124
  • [4] InBr3-Catalyzed conjugate addition of Indoles to p-quinones:: An efficient synthesis of 3-indolylquinones
    Yadav, JS
    Reddy, BVS
    Swamy, T
    SYNTHESIS-STUTTGART, 2004, (01): : 106 - 110
  • [5] ADDITION OF DITHIOCARBOXYLIC ACID DERIVATIVES TO P-QUINONES
    KLEMM, K
    GEIGER, B
    ANNALEN DER CHEMIE-JUSTUS LIEBIG, 1969, 726 (AUG): : 103 - &
  • [6] Ionic liquids-promoted addition of arylsulfinic acids to p-quinones:: A green synthesis of diaryl sulfones
    Yadav, JS
    Reddy, BVS
    Swamy, T
    Ramireddy, N
    SYNTHESIS-STUTTGART, 2004, (11): : 1849 - 1853
  • [7] The synthesis and biological evaluation of A-ring substituted steroidal p-quinones
    Milic, DR
    Gasic, MJ
    Muster, W
    Csanadi, JJ
    Solaja, BA
    TETRAHEDRON, 1997, 53 (41) : 14073 - 14084
  • [9] Recent progress in the synthesis of p-quinones and p-dihydro-quinones through oxidation of phenol derivative.: A review
    Akai, S
    Kita, Y
    ORGANIC PREPARATIONS AND PROCEDURES INTERNATIONAL, 1998, 30 (06) : 603 - +
  • [10] NUCLEOPHILIC 1,2-ADDITION TO CARBONYL GROUP OF P-QUINONES AND A NEW MOLECULAR REARANGEMENT OF A PENTAOXYPHOSPHORANE
    RAMIREZ, F
    KUGLER, HJ
    SMITH, CP
    TETRAHEDRON LETTERS, 1965, (04) : 261 - &