NDLI: Catalytic formal [2+2+1] synthesis of pyrroles from alkynes and diazenes via Ti(II)/Ti(IV) redox catalysis.

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Catalytic formal [2+2+1] synthesis of pyrroles from alkynes and diazenes via Ti(II)/Ti(IV) redox catalysis.

Content Provider	World Health Organization (WHO)-Global Index Medicus
Author	Gilbert, Zachary W. Hue, Ryan J. Tonks, Ian A.
Description	Country affiliation: United States Author Affiliation: Gilbert ZW ( Department of Chemistry, University of Minnesota - Twin Cities, 207 Pleasant St SE, Minneapolis, Minnesota 55455, USA.); Hue RJ ( Department of Chemistry, University of Minnesota - Twin Cities, 207 Pleasant St SE, Minneapolis, Minnesota 55455, USA.); Tonks IA ( Department of Chemistry, University of Minnesota - Twin Cities, 207 Pleasant St SE, Minneapolis, Minnesota 55455, USA.)
Abstract	Pyrroles are structurally important heterocycles. However, the synthesis of polysubstituted pyrroles is often challenging. Here, we report a multicomponent, Ti-catalysed formal [2+2+1] reaction of alkynes and diazenes for the oxidative synthesis of penta- and trisubstituted pyrroles: a nitrenoid analogue to classical Pauson-Khand-type syntheses of cyclopentenones. Given the scarcity of early transition-metal redox catalysis, preliminary mechanistic studies are presented. Initial stoichiometric and kinetic studies indicate that the mechanism of this reaction proceeds through a formally Ti(II)/Ti(IV) redox catalytic cycle, in which an azatitanacyclobutene intermediate, resulting from [2+2] alkyne + Ti imido coupling, undergoes a second alkyne insertion followed by reductive elimination to yield pyrrole and a Ti(II) species. The key component for catalytic turnover is the reoxidation of the Ti(II) species to a Ti(IV) imido via the disproportionation of an Î·(2)-diazene-Ti(II) complex.
File Format	HTM / HTML
ISSN	17554330
Issue Number	1
Volume Number	8
e-ISSN	17554349
Journal	Nature Chemistry
Language	English
Publisher	Nature Publishing Group
Publisher Date	2016-01-01
Publisher Place	Great Britain (UK)
Access Restriction	One Nation One Subscription (ONOS)
Subject Keyword	Discipline Chemistry Alkynes Chemistry Imides Pyrroles Chemical Synthesis Titanium Catalysis Molecular Structure Oxidation-reduction Journal Article Research Support, N.i.h., Extramural Research Support, Non-u.s. Gov't Research Support, U.s. Gov't, Non-p.h.s.
Content Type	Text
Resource Type	Article
Subject	Chemistry Chemical Engineering

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