A new cascade halosulfonylation of 1,7-enynes toward 3,4-dihydroquinolin-2(1H)-ones via sulfonyl radical-triggered addition/6-exo-dig cyclization

作者：Zhu, Yi-Long; Jiang, Bo^*; Hao, Wen-Juan; Wang, Ai-Fang; Qiu, Jiang-Kai; Wei, Ping^*; Wang, De-Cai; Li, Guigen; Tu, Shu-Jiang^*

来源：Chemical communications, 2016, 52(9): 1907-1910.

DOI：10.1039/c5cc08895j

• C-S BOND
• TERMINAL ALKYNES
• CATALYZED ARYLSULFONYLATION
• AEROBIC DIFUNCTIONALIZATION
• STEREOSELECTIVE-SYNTHESIS
• EFFICIENT SYNTHESIS
• VINYL SULFONES
• ALKENES
• SULFONYLHYDRAZIDES
• OXINDOLES

A new cascade three-component halosulfonylation of 1,7-enynes for efficient synthesis of densely functionalized 3,4-dihydroquinolin-2(1H)-ones has been established from readily accessible arylsulfonyl hydrazides and NIS (or NBS). The reaction pathway involves in situ-generated sulfonyl radical-triggered alpha,beta-conjugated addition/6-exo-dig cyclization/radical coupling sequence, resulting in continuous multiple bond-forming events including C-S, C-C and C-I (or C-Br) bonds to rapidly build up molecular complexity.

• 出版日期2016
• 单位南京大学