An efficient rhodium catalyzed direct arylation of α-diazoimines, generated from readily accessible 1,2,3-triazole, has been accomplished for the synthesis of 2,2-diaryl enamides. The reaction involves the chemo- and regioselective insertion of rhodium azavinyl carbene into aromatic C(sp 2)-H bonds. Utility of the developed methodology was demonstrated in the synthesis of indole and tetrahydroisoquinoline frameworks. © 2014 American Chemical Society.

Pazhamalai Anbarasan

Department Of Chemistry

IIT Madras is a public technical and research university located in Chennai, Tamil Nadu. Founded in 1959, it is recognised as an Institute of National Importance.

IIT Madras has been ranked as the top engineering institute in India for four years in a row by the National Institutional Ranking Framework of the MHRD

It currently offers undergraduate, postgraduate and research degrees across 16 disciplines in Engineering, Sciences, Humanities and Management. About 596 faculty belonging to science and engineering departments and centres of the Institute are engaged in teaching, research and industrial consultancy.

IIT Madras

Organic Letters

An efficient tandem rhodium(II)/squaramide relay catalysis of readily accessible indole derivatives and N-sulfonyl-1,2,3-triazoles has been developed for the enantioselective synthesis of dihydro-β-carbolines in good yield and enantioselectivity. The developed reaction involves selective insertion of in situ generated azavinyl rhodium carbene onto the C3-H bond of indole derivatives and subsequent squaramide-catalyzed enantioselective intramolecular aza-Michael reaction. Furthermore, the potential of the strategy was demonstrated through the ready conversion to potent tetrahydro-β-carbolines and the tetracyclic alkaloid core structure. © 2019 American Chemical Society.

Tandem Rh(II) and Chiral Squaramide Relay Catalysis: Enantioselective Synthesis of Dihydro-β-carbolines via Insertion to C-H Bond and Aza-Michael Reaction

An efficient rhodium-catalyzed unprecedented oxa-[2,3]-sigmatropic rearrangement of sulfur ylide derived from α-thioesters/ketones and diazo carbonyl compounds has been accomplished for the synthesis of various sulfur-tethered vinylogous carbonates in good to excellent yields. Important features of the developed reaction include wide functional group tolerance, excellent chemo- and regioselectivity, and efficient rearrangement involving the carbonyl motif. The present reaction also equally works well with α-selenoesters for the synthesis of seleno-containing vinylogous carbonates. Copyright © 2019 American Chemical Society.

Rhodium-Catalyzed Rearrangement of S/Se-Ylides for the Synthesis of Substituted Vinylogous Carbonates

An efficient cobalt(III)-catalyzed intramolecular cross-dehydrogenative C−H/N−H coupling of ortho-alkenylanilines has been developed utilizing O2as a terminal oxidant. The developed reaction tolerates various reactive functional groups and allows the synthesis of diverse indole derivatives in good to excellent yields. The method was successfully extended to the synthesis of benzofurans through the intramolecular cross-dehydrogenative C−H/O−H coupling of ortho-alkenylphenols. © 2016 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim

Chemistry - A European Journal

Cobalt(III)-Catalyzed Intramolecular Cross-Dehydrogenative C−H/X−H Coupling: Efficient Synthesis of Indoles and Benzofurans

An iodine(iii)-mediated, group-selective oxidative rearrangement of β,β-diarylenamines to α-amino ketones has been accomplished with excellent yield. The developed reaction involves the initial oxidation of enamine to an α-acyloxyimine intermediate and concomitant semipinacol rearrangement. © The Royal Society of Chemistry.

Fulltext

Chemical Communications

An iodine(iii) mediated oxidative rearrangement of enamines: efficient synthesis of α-amino ketones

A general and efficient one-pot aminoethylation of substituted indoles/pyrroles was accomplished for the synthesis of various tryptamine derivatives employing a combination of alkynes and sulfonyl azides as readily accessible aminoethylating agents. The reaction features a successful integration of copper-catalyzed alkyne and azide cycloaddition to N-sulfonyl-1,2,3-triazole, rhodium-catalyzed selective insertion of α-iminocarbenes onto the C3-H bond of indoles, and reduction of the resultant enamides to tryptamine derivatives employing either NaCNBH3 or palladium catalyst, in one-pot. The reaction also showed excellent functional-group tolerance and allowed the synthesis of various substituted tryptamines in good to excellent yield. This transformation constitutes a one-pot formal regioselective functionalization of terminal alkynes. Utility of the synthesized tryptamine was further demonstrated in the synthesis of dihydro-β-carboline and tryptoline. © 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Journal	Data powered by TypesetOrganic Letters
Publisher	Data powered by TypesetAmerican Chemical Society
ISSN	15237060
Open Access	No