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Rhodium‐Catalyzed Desulfination of Sodium Arenesulfinates and Oxidative Annulation with Alkynes
Author(s) -
Wang Hui,
Wang Yuyuan,
Yang Haijun,
Tan Chunyan,
Jiang Yuyang,
Zhao Yufen,
Fu Hua
Publication year - 2015
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201400930
Subject(s) - annulation , chemistry , rhodium , intramolecular force , catalysis , aryl , oxidative phosphorylation , intermolecular force , combinatorial chemistry , organic chemistry , molecule , biochemistry , alkyl
Polycyclic aromatic compounds are widely used in materials science, so it is highly desirable to develop an efficient and practical approach to them. In this paper, a novel, efficient and practical method for the rhodium(III)‐catalyzed desulfination of sodium arenesulfinates and oxidative annulation with alkynes has been developed, and the corresponding polycyclic aromatic compounds with multiple substituents were prepared in moderate to good yields. The reactions proceeded through sequential rhodium(III)‐catalyzed desulfination, intermolecular addition of aryl‐Rh(III) complexes to dialkyl but‐2‐ynedioates and diarylalkynes, and intramolecular oxidative annulation via CH activation. The present method is the first example of the oxidative annulation of arene derivatives with two different alkynes. Therefore, it should afford a useful strategy for the synthesis of polycyclic aromatic compounds.