A versatile and site-selective rhodium(III)-catalyzed aerobic oxidative alkenylation of arylacetamides including primary, secondary, and tertiary amides having a weak O-coordinating acetamide directing group with alkenes is described. In the reaction, air was utilized as a sole oxidant. The reaction was compatible with activated alkenes and maleimides. © 2019 American Chemical Society.

Masilamani Jeganmohan

Department Of Chemistry

Subramanian Jambu

Ramakrishnan Sivasakthikumaran

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

Transition-metal-catalyzed direct C−H bond activation reactions have been embraced as a powerful synthetic tool to access diverse functionalized arenes. However, site-selective incorporation of multiple distinct functionalities in an arene has always been a formidable challenge. Recent efforts from the synthetic community have disclosed a few dynamic synthetic approaches to fabricate multifunctionalized arenes in one-pot using a single catalytic system. These reports manifested the immense potential of such approaches to expedite contemporary organic synthesis towards building molecular complexity. In this minireview, we have illustrated the recent progress in this area, highlighting the contribution from several synthetic chemists including our group. © 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim

Chemistry - An Asian Journal

Recent Advancements in Transition-Metal-Catalyzed One-Pot Twofold Unsymmetrical Difunctionalization of Arenes

Maleimide and succinimide core moieties are present in various natural products and pharmaceuticals. In addition, these derivatives can be readily modified into biologically important organic molecules including pyrrolidines and γ-lactams. A transition-metal-catalyzed chelation-assisted functionalization of inert C−H bond of organic molecules with electrophiles or nucleophiles is one of the efficient methods to construct chemical bonds in a highly atom- and step-economical manner. The present review describes the recent advances in the reaction involving maleimides with organic molecules by a chelation-assisted inert C−H bond activation methodology. The reaction involving maleimides with organic molecules having directing groups, such as ketone, acyl, pyridyl, pyrimidyl, oxime, amide, imidate, chromone, azo, N-sulfonyl ketimine, carboxylic acids, and aldimines, were described. The scope, limitation and mechanistic investigation of the alkylation, annulation and alkenylation reactions were discussed elaborately. This review article includes the entire report on the chemical bond-forming reaction of maleimides with organic molecules by the C−H bond activation strategy until the end of 2018. © 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim

Asian Journal of Organic Chemistry

Alkylation, Annulation, and Alkenylation of Organic Molecules with Maleimides by Transition-Metal-Catalyzed C-H Bond Activation

Aerobic Oxidative Alkenylation of Weak O-Coordinating Arylacetamides with Alkenes via a Rh(III)-Catalyzed C-H Activation

The C-H alkylation of arylacetamides with activated alkenes such as substituted acrylates and vinyl sulphone in the presence of a ruthenium catalyst and organic acid via the weak O-coordination under the redox free version is described. The present protocol was effective with different substituted arylacetamides including secondary and tertiary amides. The reaction mechanism including the ortho C-H bond activation, migratory insertion, and protonation by acetic acid was suggested and supported by the deuterium labeling experiments, competitive experiments, and DFT calculations including TS analysis. Copyright © 2019 American Chemical Society.

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