Synthesis of Azo-Substituted Bicyclo[1.1.1]pentanes (BCPs) via Base-Promoted Halogen Atom Transfer

Yanchuang Zhao; Jing Zhang; Zhi-Jin Zhan; Qiujin Fan; Xu-Qiong Xiao; Ying Bai; Shao-Fei Ni; Xinxin Shao

doi:10.1021/acs.orglett.4c01546

Synthesis of Azo-Substituted Bicyclo[1.1.1]pentanes (BCPs) via Base-Promoted Halogen Atom Transfer

Org Lett. 2024 May 24;26(20):4406-4410. doi: 10.1021/acs.orglett.4c01546. Epub 2024 May 14.

Authors

Yanchuang Zhao¹, Jing Zhang¹, Zhi-Jin Zhan², Qiujin Fan¹, Xu-Qiong Xiao¹, Ying Bai¹, Shao-Fei Ni², Xinxin Shao¹

Affiliations

¹ College of Material, Chemistry and Chemical Engineering, Key Laboratory of Organosilicon Chemistry and Material Technology of Ministry of Education, Hangzhou Normal University, Hangzhou 311121, P. R. China.
² Department of Chemistry and Key Laboratory for Preparation and Application of Ordered Structural Materials of Guang-dong Province, Shantou University, Shantou 515063, P. R. China.

PMID: 38742800
DOI: 10.1021/acs.orglett.4c01546

Abstract

Because of the three-dimensional bioisosteric feature, bicyclo[1.1.1]pentylamines (BCPAs) are valuable scaffolds in synthetic chemistry and medicinal chemistry. Here, we report a Halogen Atom Transfer (XAT) mediated radical C-N coupling between C3-iodo-BCPs and diazonium salts in the presence of base. Similarly, a multicomponent reaction (MCR) enables the simultaneous construction of the C-C bond and C-N bond simultaneously. Versatile roles of diazonium salts were also explored.