Tridentate Nickel(II)-Catalyzed Chemodivergent C–H Functionalization and Cyclopropanation: Regioselective and Diastereoselective Access to Substituted Aromatic Heterocycles

A Schiff-base nickel­(II)-phosphene-catalyzed chemodivergent C–H functionalization and cyclopropanation of aromatic heterocycles is reported in moderate to excellent yields and very good regioselectivity and diastereoselectivity. The weak, noncovalent interaction between the phosphene ligand and Ni...

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Bibliographic Details
Published in:Organic letters 2020-08, Vol.22 (16), p.6313-6318
Main Authors: Nag, Ekta, Gorantla, Sai Manoj N. V. T, Arumugam, Selvakumar, Kulkarni, Aditya, Mondal, Kartik Chandra, Roy, Sudipta
Format: Article
Language:English
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Summary:A Schiff-base nickel­(II)-phosphene-catalyzed chemodivergent C–H functionalization and cyclopropanation of aromatic heterocycles is reported in moderate to excellent yields and very good regioselectivity and diastereoselectivity. The weak, noncovalent interaction between the phosphene ligand and Ni center facilitates the ligand dissociation, generating the electronically and coordinatively unsaturated active catalyst. The proposed mechanisms for the reported reactions are in good accord with the experimental results and theoretical calculations, providing a suitable model of stereocontrol for the cyclopropanation reaction.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.0c02138