[Pd]-Catalyzed para-selective allylation of phenols: access to 4-[(E)-3-aryl/alkylprop-2-enyl]phenols

Chinnabattigalla, S. and Choudhury, A. and Gedu, S. (2021) [Pd]-Catalyzed para-selective allylation of phenols: access to 4-[(E)-3-aryl/alkylprop-2-enyl]phenols. Organic and Biomolecular Chemistry, 19 (38). pp. 8259-8263. ISSN 14770520

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Abstract

4-[(E)-3-Arylprop-2-enyl]phenols are omnipresent scaffolds and constitute natural products and biologically significant compounds. Obtusastyrene and obtustyrene are two such phenolic-based natural products isolated from Dalbergia retusa. The development of strategies based on a site-selective allylation, particularly protecting group-free substrates and non-activated coupling agents, is indispensable in organic synthesis. Herein, we present a highly regioselective [Pd]-catalyzedpara-allylation of phenols using simple, inactivated allylic alcohols as allylating coupling partners. Notably, this strategy is successful in open-air and under mild reaction conditions. Besides, the efficacy of the present protocol was demonstrated by the direct synthesis of obtusastyrene and obtustyrene.

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IITH Creators:

IITH Creators	ORCiD
Satyanarayana, Gedu	https://orcid.org/ 0000-0002-6410-5421

Item Type:

Article

Uncontrolled Keywords:

Allylic alcohol; Direct synthesis; Mild reaction conditions; Natural products, Organic synthesis, Phenolics, Protecting group, Regio-selective, Simple++; Site selective

Subjects:

Chemistry

Divisions:

Department of Chemistry

Depositing User:

Mrs Haseena VKKM

Date Deposited:

28 Oct 2021 11:41

Last Modified:

11 Mar 2022 10:18

URI:

http://raiithold.iith.ac.in/id/eprint/8854