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Oxidatively induced reactivity in Rh(iii)-catalyzed 7-azaindole synthesis: insights into the role of the silver additive?

Published:31 August 2022 DOI: 10.1039/D2SC01650H PMID: 36320687
Ho Ryu, Bimal Pudasaini, Dasol Cho, Sungwoo Hong and Mu-Hyun Baik

Abstract

A typical synthetic protocol for preparing 7-azaindoles involves the coupling of 2-aminopyridine and alkyne substrates using a Rh(III)-catalyst. The catalysis requires the assistance of an external Ag+ oxidant that is thought to regenerate the catalyst and increase the turnover efficiency. Density functional theory (DFT) simulations confirm that Ag+ can oxidize various neutral Rh(III) intermediates encountered at different stages of the catalysis. Among them, the catalytically relevant species is a cationic Rh(III)-pyridyl+ complex (2A), which undergoes C–H activation of pyridine and couples an internal alkyne substrate into the pyridyl ligand to form the desired 7-azaindole product. Computations reveal that the oxidation also accelerates the reaction steps, including C–H activation via concerted metalation deprotonation (CMD), 1,2-alkyne insertion, and reductive elimination, thus highlighting the role of Ag+ as a catalytic promoter for the oxidatively induced reactivity of the Rh-catalyst in 7-azaindole synthesis. DFT calculations show that the catalysis is inefficient without invoking an oxidatively induced reaction pathway.

Substances (5)

Related products
Procduct Name CAS Molecular Formula Supplier Price
7-Azaindole 271-63-6 C7H6N2 692 suppliers $4.00-$2780.00
2-Aminopyridine 504-29-0 C5H6N2 651 suppliers $5.00-$1869.00
Silver 7440-22-4 Ag 488 suppliers $29.00-$9280.00
Rhodium(III) Chloride 10049-07-7 Cl3Rh 228 suppliers $55.00-$6550.00
Chromeo 494 Alkyne 3 suppliers Inquiry

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