Synlett 2017; 28(12): 1432-1436
DOI: 10.1055/s-0036-1588983
letter
© Georg Thieme Verlag Stuttgart · New York

Catalytic Synthesis of Chiral Phosphole Oxides via Desymmetric C–H Arylation of o-Bromoaryl Phosphine Oxides

Yan Lin, Wei-Yang Ma, Qiao-Ying Sun, Yu-Ming Cui*, Li-Wen Xu*
  • Key Laboratory of Organosilicon Chemistry and Material Technology of Ministry of Education, Hangzhou Normal University, Hangzhou 311121, P. R. of China   Email: ym_cui@hznu.edu.cn   Email: liwenxu@hznu.edu.cn
Supported by: National Natural Science Foundation of China Grant / Award numbers ‘51303043’, ‘21472031’, ‘21503060’
Supported by: Science and Technology Department of Zhejiang Province Grant / Award number ‘2015C31138’
Further Information

Publication History

Received: 08 February 2017

Accepted after revision: 05 March 2017

Publication Date:
11 April 2017 (eFirst)

Abstract

A palladium-catalyzed intramolecular direct arylation reaction of o-bromoaryl phosphine oxides was developed to afford a variety of P-stereogenic phosphole oxides in good yields. The enantioselectivities were closely associated with the specific structures of substrates, which ranged from 4–94%. As a result of ready availability of starting materials and simple operation to improve the enantioselectivities of the products with low ee values, the method provides a simple and straightforward procedure for the synthesis of P-stereogenic phosphole oxides.

Supporting Information