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Org Lett. 2015 Dec 18;17(24):6078-81. doi: 10.1021/acs.orglett.5b03100. Epub 2015 Nov 30.

Catalytic Arylsulfonyl Radical Triggered 1,7-Enyne Bicyclizations.

Zhu YL1,2, Jiang B2,3, Hao WJ2, Qiu JK1,2, Sun J1,2, Wang DC1, Wei P1, Wang AF2, Li G3,4, Tu SJ2.

Author information

1
Biotechnology and Pharmaceutical Engineering, Nanjing Tech University , Nanjing 210009, Jiangsu P. R. China.
2
School of Chemistry and Chemical Engineering, and Jiangsu Key Laboratory of Green Synthetic Chemistry for Functional Materials, Jiangsu Normal University , Xuzhou, 221116, Jiangsu P. R. China.
3
Department of Chemistry and Biochemistry, Texas Tech University , Lubbock, Texas 79409-1061, United States.
4
Institute of Chemistry & BioMedical Sciences, Nanjing University , Nanjing 210093, P. R. China.

Abstract

A new metal-free bicyclization reaction of 1,7-enynes anchored by α,β-conjugates with arylsulfonyl radicals generated in situ from sulfonyl hydrazides has been established using tert-butyl hydroperoxide and tetrabutylammonium iodide. The reactions occurred through sulfonylation/6-exo-dig/6-exo-trig bicyclization/in situ desulfonylation/5-exo-trig cyclization/alkyl or alkenyl migration cascade mechanism to give benzo[j]phenanthridines regioselectively.

PMID:
26618403
DOI:
10.1021/acs.orglett.5b03100
[Indexed for MEDLINE]

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