Synthesis of β,β-Dithioketones by Merging C-C and C-S Bond Cleavage in [1 + 1 + 1 + 1 + 1 + 1] Annulation

Dong-Sheng Yang; Xiang-Long Chen; Chun-Yan Wu; Bo-Cheng Tang; Yong-Cheng Xiao; Yan-Dong Wu; An-Xin Wu

doi:10.1021/acs.orglett.4c01364

Synthesis of β,β-Dithioketones by Merging C-C and C-S Bond Cleavage in [1 + 1 + 1 + 1 + 1 + 1] Annulation

Org Lett. 2024 May 24;26(20):4340-4345. doi: 10.1021/acs.orglett.4c01364. Epub 2024 May 14.

Authors

Dong-Sheng Yang¹, Xiang-Long Chen¹, Chun-Yan Wu¹, Bo-Cheng Tang², Yong-Cheng Xiao¹, Yan-Dong Wu¹, An-Xin Wu^{1

3}

Affiliations

¹ National Key Laboratory of Green Pesticide, International Joint Research Center for Intelligent Biosensor Technology and Health, College of Chemistry, Central China Normal University, Wuhan, Hubei 430079, China.
² State Key Laboratory of Chemical Biology and Drug Discovery, Department of Applied Biology and Chemical Technology, The Hong Kong Polytechnic University, Kowloon, Hong Kong SAR, China.
³ State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000, P. R. China.

PMID: 38743916
DOI: 10.1021/acs.orglett.4c01364

Abstract

An unconventional [1 + 1 + 1 + 1 + 1 + 1] annulation process was developed for the construction of β,β-dithioketones by merging C-C and C-S bond cleavage. In this reaction, rongalite concurrently served as triple C1 units, dual sulfur(II) synthons, and a reductant for the first time. Mechanism investigation indicated that the reaction involved the self-mediated valence state change of rongalite. By performing this step-economical method, the challenging construction of C₅-substituted 1,3-dithiane can be achieved under mild and simple conditions.