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Nickel‐Promoted Oxidative ipso ‐Annulation of N ‐( p ‐Methoxyaryl)propiolamides with α ‐Carbonyl Alkyl Bromides
Author(s) -
Li Meng,
Song RenJie,
Li JinHeng
Publication year - 2017
Publication title -
chinese journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.28
H-Index - 41
eISSN - 1614-7065
pISSN - 1001-604X
DOI - 10.1002/cjoc.201600749
Subject(s) - chemistry , annulation , alkyl , alkyne , medicinal chemistry , oxidative cleavage , cleavage (geology) , nickel , bond cleavage , oxidative phosphorylation , oxidative addition , stereochemistry , organic chemistry , catalysis , geotechnical engineering , fracture (geology) , engineering , biochemistry
A new route to producing 3‐alkyl spiro[4,5]trienones via nickel‐promoted radical oxidative ipso ‐annulation of N ‐( p ‐methoxyaryl)propiolamides with α ‐carbonyl alkyl bromides using TBHP oxidant is described. The method allows the formation of three new C—C bonds through a sequence of oxidative C—Br bond cleavage, ipso ‐cyclization and dearomatization, and represents a new alkyne 1,2‐difunctionalization to access to the construction of spiro[4,5]trienones.