Journal
ADVANCED SYNTHESIS & CATALYSIS
Volume 355, Issue 10, Pages 1948-1954Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.201300346
Keywords
[3+2]cyclization; diazo compounds; gold catalysis; nitriles; pyrroles
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Funding
- Ministerio de Economia y Competitividad of Spain (MINECO) [CTQ2010-20517-C02-01]
- MINECO
- European Union (Fondo Social Europeo)
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The reaction of nitriles with alkenyldiazo compounds in the presence of gold catalysts provides functionalized pyrrole derivatives in moderate to high yields. This formal [3+2] cyclization reaction takes place with complete regioselectivity. The observed regiochemical outcome suggests the attack of the nitrile to the terminal position of the alkenylgold carbenoid (vinylogous reactivity). A broad range of nitriles (including those bearing functional groups) is compatible with this cyclization reaction.
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