Cu-Mediated Sulfonyl Radical-Enabled 5- exo-trig Cyclization of Alkenyl Aldehydes: Access to Sulfonylmethyl 1 H-Indenes

Jiabin Ni; Yu Xue; Liping Sun; Ao Zhang

doi:10.1021/acs.joc.8b00341

Cu-Mediated Sulfonyl Radical-Enabled 5- exo-trig Cyclization of Alkenyl Aldehydes: Access to Sulfonylmethyl 1 H-Indenes

J Org Chem. 2018 Apr 20;83(8):4598-4605. doi: 10.1021/acs.joc.8b00341. Epub 2018 Apr 6.

Authors

Jiabin Ni^{1

2

3}, Yu Xue^{1

2

4}, Liping Sun⁴, Ao Zhang^{1

2

3}

Affiliations

¹ CAS Key Laboratory of Receptor Research , Shanghai Institute of Materia Medica (SIMM), Chinese Academy of Sciences , Shanghai 201203 , China.
² State Key Laboratory of Drug Research , Shanghai Institute of Materia Medica (SIMM), Chinese Academy of Sciences , Shanghai 201203 , China.
³ University of Chinese Academy of Sciences , Beijing 100049 , China.
⁴ Department of Medicinal Chemistry , China Pharmaceutical University , Nanjing 210009 , China.

PMID: 29589947
DOI: 10.1021/acs.joc.8b00341

Abstract

An efficient method for the construction of sulfonylmethyl 1 H-indenes via Cu(I)-mediated sulfonyl radical-enabled 5- exo-trig cyclization of alkenyl aldehydes has been developed for the first time. Mechanistic studies indicated that a radical addition-cyclization-elimination (RACE) process might be involved. The reaction features a relatively broad substrate scope, good annulation efficiency, and varying functional group tolerance.

Publication types

Research Support, Non-U.S. Gov't