Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 77, Issue 3, Pages 1217-1232Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo201866c
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Funding
- EU
- University of Nottingham
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In a new variation on the Fischer indole synthesis, readily available haloarenes are converted into a wide range of indoles in just two steps by halogen-magnesium exchange and quenching with di-tert-butyl azodicarboxylate, followed by reaction with aldehydes or ketones under acidic conditions. The protocol, which is readily extended to the preparation of indole isosteres, 4- and 6-azaindoles and thienopyrroles, obviates the need to prepare potentially toxic aryl hydrazines, simultaneously avoiding undesirable anilines such as naphthylamines.
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