A general palladium-catalyzed aryl(alkyl)thiolation of various substituted unactivated arenes is accomplished for the synthesis of diverse unsymmetrical diaryl(alkyl) sulfides in good yield employing electrophilic sulfur reagent 6 derived from succinimide. The developed strategy was coupled with intramolecular arylation of a C-H bond to afford dibenzothiphene derivatives, an important moiety in material science as organic semiconductors. © 2014 American Chemical Society.

Pazhamalai Anbarasan

Department Of Chemistry

Perumal Saravanan

dyes, reagents, indicators, markers and buffers

Palladium

succinimide derivative

article

catalysis

chemical structure

chemistry

hydrogen bond

Hydrogen Bonding

Indicators and Reagents

Molecular Structure

Succinimides

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 and chemodivergent palladium-catalyzed thiolation (C-S) and imidation (C-N) of directing group-assisted C-H bonds have been accomplished employing N-(arylthio)imides in combination with either Brønsted acid or Lewis acid, respectively. Notable features of the developed methodologies include excellent diversity, high functional group tolerance, wide substrate scope, and use of a single N-S reagent. Importantly, the developed hypothesis was also successfully extended to the amidation of C-H bonds. A plausible mechanistic pathway was proposed based on the preliminary mechanistic study. © 2018 American Chemical Society.

Lewis Acid/Brønsted Acid Controlled Pd(II)-Catalyzed Chemodivergent Functionalization of C(sp2)-H Bonds with N-(Arylthio)i(a)mides

Efficient and general copper catalyzed oxidative cyclization of ortho-vinylaniline has been accomplished employing N-tosylhydrazone as coupling partner. Various substituted quinoline derivatives of biological importance were achieved in good to excellent yield. The important features are the high functional group tolerates, up-gradation to gram scale synthesis and possible one-pot synthesis of quinoline from corresponding carboxaldehyde. Synthetic potential of the obtained quinoline derivatives was demonstrated through C-H bond functionalization reaction. Furthermore, preliminary mechanistic investigation revealed the possible generation of non-stabilized diazo compound and imine derivative as potential intermediates as well as copper catalyzed electrocyclic reaction and oxidative aromatization. © 2018 Elsevier Inc.

Journal of Catalysis

Copper catalyzed oxidative coupling of ortho-vinylanilines with N-tosylhydrazones: Efficient synthesis of polysubstituted quinoline derivatives

Efficient and selective rhodium-catalyzed cyanation of chelation-assisted C-H bonds of alkenes has been accomplished using environmentally benign N-cyano-N-phenyl-p-methylbenzenesulfonamide (NCTS) as a cyanating reagent. The developed methodology tolerates various functional groups and allows the synthesis of diverse substituted acrylonitriles in good to excellent yields. Furthermore, the potential of the methodology was demonstrated through the formal synthesis of chlorpheniramine-based antagonist. © 2015 American Chemical Society.

Rhodium-Catalyzed Cyanation of C(sp2)-H Bond of Alkenes

Angewandte Chemie International Edition

Palladium-Catalyzed Direct Synthesis of Phosphole Derivatives from Triarylphosphines through Cleavage of Carbon-Hydrogen and Carbon-Phosphorus Bonds

The Journal of Organic Chemistry

Cu-Catalyzed Synthesis of Diaryl Thioethers and S-Cycles by Reaction of Aryl Iodides with Carbon Disulfide in the Presence of DBU

ChemInform

Catalytic Direct Arylation with Aryl Chlorides, Bromides, and Iodides: Intramolecular Studies Leading to New Intermolecular Reactions.

Journal of the American Chemical Society

Cu(II)-Catalyzed Functionalizations of Aryl C−H Bonds Using O2as an Oxidant

Chemical Reviews

Ru-, Rh-, and Pd-Catalyzed C−C Bond Formation Involving C−H Activation and Addition on Unsaturated Substrates:  Reactions and Mechanistic Aspects

Palladium catalyzed aryl(alkyl)thiolation of unactivated arenes

Journal	Organic Letters
ISSN	15237060
Open Access	No