In:
Advanced Synthesis & Catalysis, Wiley, Vol. 361, No. 23 ( 2019-12-03), p. 5340-5345
Abstract:
A novel radical‐induced annulation/1,8‐halosulfonylation of β‐alkynyl ketones with haloaryl diazonium tetrafluoroborates and DABCO . bis(sulfur dioxide) was first achieved via the cleavage/recombination of C( sp 3 )−C( sp 3 ) and C( sp 2 )‐halogen bonds, from which 47 examples of sulfone‐containing 1,3‐dimethylene‐substituted ( Z , Z )‐isobenzofurans as single stereoisomers were synthesized in generally good yields. This multicomponent pathway is proposed to proceed through the in‐situ generation of arylsulfonyl radicals, followed by selective radical addition‐cyclization and ring‐opening of the cyclopropyl unit as well as C( sp 2 )‐halogen bond cleavage, resulting in the consecutive construction of three new chemical bonds, including C−S, C−O and C‐halogen bonds. magnified image
Type of Medium:
Online Resource
ISSN:
1615-4150
,
1615-4169
DOI:
10.1002/adsc.v361.23
DOI:
10.1002/adsc.201900729
Language:
English
Publisher:
Wiley
Publication Date:
2019
detail.hit.zdb_id:
2041384-1
detail.hit.zdb_id:
2033084-4
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