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Highly Site-Selective Direct C−H Bond Functionalization of Unactivated Arenes with Propargyl α‑Aryl-α-diazoacetates via Scandium Catalysis

preprint
submitted on 19.04.2021, 16:41 and posted on 20.04.2021, 12:48 by Balu S. Navale, Debasish Laha, Subhrashis Banerjee, Kumar Vanka, Prof. Dr. Ramakrishna G. Bhat

Highly chemo- and regio-selective C–H bond functionalization of unactivated arenes with propargyl α-aryl-α-diazoacetates is developed using scandium catalysis. Variety of unactivated, mildly deactivated and electronically activated arenes are functionalized using this protocol. We have explored the novel combination of scandium triflate and propargyl α-aryl-α-diazoacetate as catalyst-reagent system for the effective C–H bond functionalization. The protocol avoids the use of expensive catalysts and practicality of the protocol has been demonstrated by the gram scale synthesis of very useful α-diarylacetates including antispasmodic drug-adephenine.

Funding

DST-SERB (CRG/2019/005753) and (EMR/2015/000909), New Delhi, Govt. of India for the generous research grant.

History

Email Address of Submitting Author

rgb@iiserpune.ac.in

Institution

Indian Institute of Science Education and Research (IISER) Pune

Country

India

ORCID For Submitting Author

0000-0002-7739-9553

Declaration of Conflict of Interest

There are no conflicts to declare.

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