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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 44, 2014 - Issue 13
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Original Articles

Palladium-Catalyzed Direct C-3 Alkynylation of Indolizines with (2,2-Dibromovinyl)arenes

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Pages 1970-1977 | Received 07 Dec 2013, Published online: 29 May 2014
 

Abstract

The direct C-3 alkynylation of indolizines with (2,2-dibromovinyl)arenes in the presence of palladium catalyst has been developed. This novel protocol showed wide substrate scope with respect to both indolizines and dibromoalkenes. Also this method was characterized with high efficiency and good functional group tolerance.

GRAPHICAL ABSTRACT

Notes

a All reactions were run with indolizine-1-carbonitrile (0.3 mmol), (2,2-dibromovinyl) benzene (0.9 mmol), catalyst (0.03 mmol), ligand (0.06 mmol), base (0.9 mmol), and solvent (2 mL), at 100 °C for 24 h under N2.

b DPEPhos = oxybis(2,1-phenylene)bis(diphenylphosphine).

c Isolated yields of alkynylation.

d When AgOAc (2 equiv) was added.

a Reaction conditions: Indolizines (0.3 mmol), (2,2-dibromovinyl)benzene (0.9 mmol), Pd(OAc)2 (0.03 mmol), DPEPhos (0.06 mmol), AgOAc (0.6 mmol), and CsOAc (0.9 mmol), DMF (2 mL), 100 °C, 24 h, N2.

b Isolated yields.

a Reaction conditions: indolizine-1-carbonitrile (0.3 mmol), (2,2-dibromovinyl)arenes (0.9 mmol), Pd(OAc)2 (0.03 mmol), DPEPhos (0.06 mmol), AgOAc (0.6 mmol), and CsOAc (0.9 mmol), DMF (2 mL), 100 °C, 24 h, N2.

b Isolated yields.

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