Work

Nickel‐Catalyzed Efficient, Regioselective One‐Pot Synthesis of 1‐Methyleneindenes via Tandem C–C Bond Formation: Computational Mechanistic Insights and Docking Studies

Year: 2025

Type: article

Abstract: Herein, we report a nickel-catalyzed tandem cyclization-coupling method for the regioselective synthesis of 1-methyleneindenes and benzofulvenes from 1-(2,2-dibromovinyl)-2-alkynylbenzenes and aryl boronic acids. The transformation proceeds in the presence of a suitable ligand and base, enabling sequential activation of the C─Br bonds and intra-molecular alkyne moiety under relatively mild reaction conditions with yields 72%-85%. This robust protocol offers wide range of functional group tolerance in substrate and boronic acid part. Density functional theory (DFT) calculations, in addition, provide thorough mechanistic insights that point to a tandem process of oxidative addition, migratory insertion, and reductive elimination, with key energetic preferences explaining the observed product selectivity.

Source: Chemistry - An Asian Journal

DOI: 10.1002/asia.70329

Authors: Sk Shamim Ahamed, Rahul Paul, Tathagata Chakraborty, Rabindranath Lo, Debashree Manna, Tapas Ghosh

Institutions: Jadavpur University, Czech Academy of Sciences, Czech Academy of Sciences, Institute of Organic Chemistry and Biochemistry

Language: English

Topic: Catalytic Cross-Coupling Reactions

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: green

Funders: Council of Scientific and Industrial Research, India, Science and Engineering Research Board

Award: G3780135010