Highly Stereoselective Synthesis of Multisubstituted Olefins from Alkynyl Tetracoordinate Borons and Iodonium Ylides via a Cyclic Intermediate

Jinchao Liang; Xin Chen; Jinglong Chen; Xingxing Ma; Qiuling Song

doi:10.1021/acs.orglett.4c01031

Highly Stereoselective Synthesis of Multisubstituted Olefins from Alkynyl Tetracoordinate Borons and Iodonium Ylides via a Cyclic Intermediate

Org Lett. 2024 May 10;26(18):3872-3877. doi: 10.1021/acs.orglett.4c01031. Epub 2024 Apr 28.

Authors

Jinchao Liang¹, Xin Chen¹, Jinglong Chen¹, Xingxing Ma², Qiuling Song^{2

3

4}

Affiliations

¹ College of Materials Science and Engineering, Fuzhou University, Fuzhou, Fujian 350108, China.
² Key Laboratory of Molecule Synthesis and Function Discovery, Fujian Province University, College of Chemistry at Fuzhou University, Fuzhou, Fujian 350108, China.
³ School of Chemistry and Chemical Engineering, Henan Normal University, Xinxiang, Henan 453007, China.
⁴ State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, China.

PMID: 38678580
DOI: 10.1021/acs.orglett.4c01031

Abstract

We developed an intriguing and practical strategy for highly stereoselective assembly of multisubstituted olefins from alkynyl tetracoordinate boron species via a cyclic intermediate with 1,2-phenyl migration. We also developed a general method for the construction of deuterated trisubstituted alkenes from a cheap deuteration source, D₂O, and the corresponding deuterated trisubstituted alkenes were obtained with excellent deuteration rates. This transformation features a novel reaction mechanism, exclusive stereoselectivity, and deuterated trisubstituted alkenes with excellent deuteration ratios.