Radical addition-polar termination cascade: efficient strategy for photoredox-neutral-catalysed cyclopropanation and Giese-type reactions of alkenyl N-methyliminodiacetyl boronates

Yongjun Liu; Wenping Luo; Jiali Wu; Yewen Fang; Yan Li; Xiaoping Jin; Li Zhang; Zongyong Zhang; Fenfen Xu; Chan Du

doi:10.1039/D0QO00349B

Radical addition-polar termination cascade: efficient strategy for photoredox-neutral-catalysed cyclopropanation and Giese-type reactions of alkenyl N-methyliminodiacetyl boronates†‡

Yongjun Liu,^a Wenping Luo,^a Jiali Wu,^b Yewen Fang,

*^b Yan Li,*^a Xiaoping Jin,*^c Li Zhang,^c Zongyong Zhang,^b Fenfen Xu^b and Chan Du^b

Author affiliations

* Corresponding authors

^a Hubei Collaborative Innovation Center for Advanced Organic Chemical Materials and Ministry-of-Education Key Laboratory for Synthesis and Application of Organic Functional Molecules, Hubei University, No. 368 Youyi Dadao, Wuhan 430062, China
E-mail: liyanok@hubu.edu.cn

^b School of Materials and Chemical Engineering, Ningbo University of Technology, No. 201 Fenghua Road, Ningbo 315211, China
E-mail: fang@nbut.edu.cn

^c Department of Pharmaceutical Engineering, Zhejiang Pharmaceutical College, No. 888 Yinxian Avenue East, Ningbo 315100, China
E-mail: jinxp@mail.zjpc.net.cn

Abstract

With radical addition-polar termination (RAPT) cascade as the strategy, efficient cyclopropanation and Giese-type reactions of alkenyl N-methyliminodiacetyl boronates have been realized by means of photoredox catalysis. With chloro- or bromomethyl silicate as the methylene source, a variety of cyclopropyl MIDA boronates as air- and chromatographically stable solids were prepared via photoredox-catalysed cyclopropanation of α-MIDA-boryl styrenes, 2-propenyl-BMIDA, and ethenyl-BMIDA. Moreover, photocatalytic Giese-type reactions of alkyl radicals with α-MIDA-boryl styrenes were also developed. It is essential for the successful radical conjugate addition employing alkyl silicates as the radical precursor. These RAPT cascades are characterized by a redox-neutral and additive-free process.

Organic Chemistry Frontiers

Radical addition-polar termination cascade: efficient strategy for photoredox-neutral-catalysed cyclopropanation and Giese-type reactions of alkenyl N-methyliminodiacetyl boronates†‡

Abstract

Supplementary files

Article information

Download Citation

Permissions

Radical addition-polar termination cascade: efficient strategy for photoredox-neutral-catalysed cyclopropanation and Giese-type reactions of alkenyl N-methyliminodiacetyl boronates

Social activity

Search articles by author

Spotlight

Advertisements