Reversed reactivity of anilines with alkynes in the rhodium-catalysed C–H activation/carbonylation tandem

Siba P. Midya, Manoj K. Sahoo, Vinod G. Landge, P. R. Rajamohanan and Ekambaram Balaraman ()
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Siba P. Midya: CSIR-National Chemical Laboratory (CSIR-NCL)
Manoj K. Sahoo: CSIR-National Chemical Laboratory (CSIR-NCL)
Vinod G. Landge: CSIR-National Chemical Laboratory (CSIR-NCL)
P. R. Rajamohanan: Central NMR Facility, CSIR-National Chemical Laboratory (CSIR-NCL)
Ekambaram Balaraman: CSIR-National Chemical Laboratory (CSIR-NCL)

Nature Communications, 2015, vol. 6, issue 1, 1-10

Abstract: Abstract Development of multicatalytic approach consisting of two or more mechanistically distinct catalytic steps using a single-site catalyst for rapid and straightforward access of structurally complex molecules under eco-benign conditions has significance in contemporary science. We have developed herein a rhodium-catalysed C–H activation strategy which uses an unprotected anilines and an electron-deficient alkynes to C–C bonded products as a potential intermediate in contrast to the archetypical C–N bonded products with high levels of regioselectivity. This is followed by carbonylation of C–H bond activated intermediate and subsequent annulation into quinolines has been described. This rhodium-catalysed auto-tandem reaction operates under mild, environmentally benign conditions using water as the solvent and CO surrogates as the carbonyl source with the concomitant generation of hydrogen gas. The strategy may facilitate the development of new synthetic protocols for the efficient and sustainable production of chemicals in an atom-economic way from simple, abundant starting materials.

Date: 2015
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DOI: 10.1038/ncomms9591

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