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Imine as a Linchpin Approach for Distal C(sp2)–H Functionalization

preprint
submitted on 06.01.2020, 05:37 and posted on 07.01.2020, 06:10 by Sukdev Bag, Sadhan Jana, Sukumar Pradhan, Suman Bhowmick, Nupur Goswami, Soumya Kumar Sinha, Debabrata Maiti

Despite the widespread applications of C–H functionalization, controlling site selectivity remains a significant challenge. Covalently attached directing group (DG) served as an ancillary ligand to ensure proximal ortho-, distal meta- and para-C-H functionalization over the last two decades. These covalently linked DGs necessitate two extra steps for a single C–H functionalization: introduction of DG prior to C–H activation and removal of DG post-functionalization. We introduce here a transient directing group for distal C(sp2)-H functionalization via reversible imine formation. By overruling facile proximal C-H bond activation by imine-N atom, a suitably designed pyrimidine-based transient directing group (TDG) successfully delivered selective distal C-C bond formation. Application of this transient directing group strategy for streamlining the synthesis of complex organic molecules without any necessary pre-functionalization at the distal position has been explored.

Funding

SERB India (CRG/2018/003951)

History

Email Address of Submitting Author

dmaiti@iitb.ac.in

Institution

Indian Institute of Technology Bombay

Country

India

ORCID For Submitting Author

0000-0001-8353-1306

Declaration of Conflict of Interest

The authors declare the following competing financial interest(s): A patent application is filed based on the work described in this manuscript

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