Nickel-catalyzed direct alkynylation of C(sp2)–H bonds of amides: an “inverse Sonogashira strategy” to ortho-alkynylbenzoic acids

Vinod G. Landge; Chinmay H. Shewale; Garima Jaiswal; Manoj K. Sahoo; Siba P. Midya; Ekambaram Balaraman

doi:10.1039/C5CY01299F

Nickel-catalyzed direct alkynylation of C(sp²)–H bonds of amides: an “inverse Sonogashira strategy” to ortho-alkynylbenzoic acids

Vinod G. Landge,^a^b Chinmay H. Shewale,^a Garima Jaiswal,^a^b Manoj K. Sahoo,^a^b Siba P. Midya^a^b and Ekambaram Balaraman*^a^b

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* Corresponding authors

^a Catalysis Division, CSIR-National Chemical Laboratory (CSIR-NCL), Dr. Homi Bhabha Road, Pune – 411008, India
E-mail: eb.raman@ncl.res.in

^b Academy of Scientific and Innovative Research (AcSIR), New Delhi – 110 025, India

Abstract

Nickel-catalyzed direct alkynylation of C(sp²)–H bonds of amides using commercially available, inexpensive 8-aminoquinoline as a removable bidentate directing group is described. The present ortho-alkynylation has a broad substrate scope, functional group tolerance and high regiocontrol, and can be scaled up. The efficiency and selectivity of this strategy provide sustainable routes to a diverse array of ortho-alkynylbenzoic acids under Ni(II)-catalyzed conditions.

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Publication details

The article was received on 08 Aug 2015, accepted on 09 Oct 2015 and first published on 23 Oct 2015

Article type: Paper

DOI: 10.1039/C5CY01299F

Author version available: Download Author version (PDF)

Citation: Catal. Sci. Technol., 2016,6, 1946-1951

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Nickel-catalyzed direct alkynylation of C(sp²)–H bonds of amides: an “inverse Sonogashira strategy” to ortho-alkynylbenzoic acids

V. G. Landge, C. H. Shewale, G. Jaiswal, M. K. Sahoo, S. P. Midya and E. Balaraman, Catal. Sci. Technol., 2016, 6, 1946
DOI: 10.1039/C5CY01299F
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Catalysis Science & Technology

Nickel-catalyzed direct alkynylation of C(sp²)–H bonds of amides: an “inverse Sonogashira strategy” to ortho-alkynylbenzoic acids

Abstract

Supplementary files

Publication details

Nickel-catalyzed direct alkynylation of C(sp²)–H bonds of amides: an “inverse Sonogashira strategy” to ortho-alkynylbenzoic acids

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