Ester-directed orthogonal dual C–H activation and ortho aryl C–H alkenylation via distal weak coordination

Bakthadoss, Manickam and Reddy, Tadiparthi Thirupathi and Agarwal, Vishal and Sharada, D S (2022) Ester-directed orthogonal dual C–H activation and ortho aryl C–H alkenylation via distal weak coordination. Chemical Communications, 58 (9). pp. 1406-1409. ISSN 1359-7345

Text
Chemical_Communications.pdf - Published Version
Restricted to Registered users only
Download (3MB) | Request a copy

Abstract

An unprecedented orthogonal cross-coupling between aromatic C(sp2) and aliphatic olefinic C(sp2) carbons of two same molecules via dual C-H bond activation in an intermolecular fashion has been developed using a distal ester-directing group. This new coupling reaction led to the synthesis of the highly functionalized 1,3-diaryl molecular architecture in very good yields and with high chemo- and regioselectivities. In addition, using ester as the distal directing group, ortho C-H olefination of α-methyl aryl acrylates and cinnamic esters with various alkenes has been achieved in very good yields and with a wide range of substrate scope. This journal is © The Royal Society of Chemistry.

[error in script]

IITH Creators:

IITH Creators	ORCiD
Sharada, D S	UNSPECIFIED

Item Type:

Article

Additional Information:

The authors thank DST-SERB (ref no.: EEQ/2018/000930) for financial support. V. A. and T. T. R. thank CSIR, New Delhi for Direct-Senior Research Fellowship (D-SRF). We thank Pondi-cherry University for NMR and ESI-HRMS facility.

Uncontrolled Keywords:

Bond activation; C-H bond; Chemo-and regioselectivities; Coupling reaction; Cross-couplings; Directing groups; Functionalized; Molecular architecture; Olefination

Subjects:

Chemistry

Divisions:

Department of Chemistry

Depositing User:

. LibTrainee 2021

Date Deposited:

14 Jul 2022 10:08

Last Modified:

14 Jul 2022 10:08

URI:

http://raiithold.iith.ac.in/id/eprint/9696