Double SO2 Insertion into 1,7-Diynes Leading to Functionalized Naphtho[1,2-c]thiophene 2,2-dioxides | Zendy

AiFang Wang | Zendy; WenJuan Hao | Zendy; YiLong Zhu | Zendy; Guigen Li | Zendy; Peng Zhou | Zendy; Bo Jiang | Zendy

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Double SO₂ Insertion into 1,7-Diynes Leading to Functionalized Naphtho[1,2-c]thiophene 2,2-dioxides

Author(s) -

AiFang Wang,

WenJuan Hao,

YiLong Zhu,

Guigen Li,

Peng Zhou,

Bo Jiang

Publication year - 2018

Publication title -

acs omega

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.779

H-Index - 40

ISSN - 2470-1343

DOI - 10.1021/acsomega.7b01789

Subject(s) - thiophene , chemistry , combinatorial chemistry , medicinal chemistry , organic chemistry

A novel metal-free double SO 2 insertion/multicomponent bicyclization cascade of benzene-linked 1,7-diynes has been established by treatment with aryldiazonium tetrafluoroborates and DABCO-bis(sulfur dioxide) under redox-neutral conditions, providing a range of dual sulfone-containing naphtho[1,2- c ]thiophene 2,2-dioxides with generally high stereoselectivity. The reaction pathway is proposed to proceed through the sequence of arylsulfonyl-radical-induced 6-exo-dig/5-endo-trig bicyclization, H-abstraction, and diazotization.

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