Abstract
The ruthenium-catalyzed ortho alkenylation of substituted aromatic and heteroaromatic nitriles with activated alkenes providing ortho alkenylated aromatic and heteroaromatic nitriles in a highly regio- and stereoselective manner is described.
Highlights
The ruthenium-catalyzed ortho alkenylation of substituted aromatic and heteroaromatic nitriles with activated alkenes providing ortho alkenylated aromatic and heteroaromatic nitriles in a highly regio- and stereoselective manner is described
Selective transformation of the C–H bond of organic moieties into C–C and C–heteroatom bond catalyzed by transition metal complexes via C–H bond activation is one of the most versatile and well-acknowledged methods in organic synthesis.[1]
A transition metal-catalyzed oxidative cross-coupling of heteroatom substituted aromatics with alkenes has proven to be a highly efficient route to synthesize disubstituted alkenes without having any prefunctionalized starting materials in a highly regio- and stereoselective manner.[3]
Summary
The ruthenium-catalyzed ortho alkenylation of substituted aromatic and heteroaromatic nitriles with activated alkenes providing ortho alkenylated aromatic and heteroaromatic nitriles in a highly regio- and stereoselective manner is described. We wish to report for the first time nitrile as a p-bond coordinating group for the ortho alkenylation of aromatic and heteroaromatic nitriles with activated alkenes in the presence of a ruthenium catalyst (Fig. 2, eqn (2)). In AgOAc, the ortho C–H bond activation takes place selectively and further reaction with n-butyl acrylate (2a) provides the ortho alkenylated benzonitrile 4aa in 75% isolated yield.
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