Iodobenzene-Mediated Intramolecular
Oxidative Coupling of Substituted 4-Hydroxyphenyl-N-phenylbenzamides for the Synthesis
of Spirooxindoles

Zhengsen Yu; Xuhui Ju; Junyan Wang; Wei Yu

doi:10.1055/s-0030-1259444

PAPER

Iodobenzene-Mediated Intramolecular Oxidative Coupling of Substituted 4-Hydroxyphenyl-N-phenylbenzamides for the Synthesis of Spirooxindoles

Zhengsen Yu, Xuhui Ju, Junyan Wang, Wei Yu*
State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou, Gansu 730000, P. R. of China
Fax: +86(931)8915557; e-Mail: yuwei@lzu.edu.cn;

Abstract

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Abstract

Phenyliodine(III) bis(trifluoroacetate) (PIFA) can effect the intramolecular oxidative coupling of substituted 4-hydroxyphenyl-N-phenylbenzamides. The transformations could be realized in a catalytic manner by using iodobenzene as catalyst and m-chloroperoxybenzoic acid or urea˙H₂O₂ as terminal oxidant. This reaction constitutes an efficient method for the synthesis of spirooxindoles.

Key words

hypervalent iodine - oxidative coupling - phenolic coupling - spirooxindoles - iodobenzene

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