Please use this identifier to cite or link to this item: http://hdl.handle.net/10397/65765
Title: Rhodium-catalyzed oxidative cycloaddition of N-tert-butoxycarbonylhydrazones with alkynes for the synthesis of functionalized pyrroles via C(sp3)–H bond functionalization
Authors: Chan, CM
Zhou, Z
Yu, WY 
Keywords: Alkynes
Cycloaddition
C–H activation
Nitrogen heterocycles
Rhodium
Issue Date: 2016
Publisher: Wiley-VCH
Source: Advanced synthesis & catalysis, 2016, v. 358, no. 24, p. 4067-4074 How to cite?
Journal: Advanced synthesis & catalysis 
Abstract: A rhodium(III)-catalyzed cycloaddition of N-tert-butoxycarbonylhydrazones with internal alkynes was developed. The reaction features a regioselective α-imino alkyl C(sp3)−H bond functionalization resulting in selective formation of highly functionalized NH-free pyrroles. Our studies showed that utilizing the N-tert-butoxycarbonyl (N-Boc) as the oxidizing directing group is critical for achieving the observed pyrrole formation versus the isoquinoline formation. To account for the pyrrole formation, we hypothesized that a prior tautomerization of the N-Boc-hydrazones to enamines should occur, followed by regioselective C(sp2)–H cleavage to form a putative five-membered rhodacycle. Subsequent coupling of the rhodacycle with the alkynes would afford the pyrrole products. (Figure presented.).
URI: http://hdl.handle.net/10397/65765
ISSN: 1615-4150
EISSN: 1615-4169
DOI: 10.1002/adsc.201600900
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