Imine as a linchpin approach for meta-C–H functionalization

Sukdev Bag, Sadhan Jana, Sukumar Pradhan, Suman Bhowmick, Nupur Goswami, Soumya Kumar Sinha and Debabrata Maiti ()
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Sukdev Bag: Indian Institute of Technology Bombay
Sadhan Jana: Indian Institute of Technology Bombay
Sukumar Pradhan: Indian Institute of Technology Bombay
Suman Bhowmick: Indian Institute of Technology Bombay
Nupur Goswami: Indian Institute of Technology Bombay
Soumya Kumar Sinha: Indian Institute of Technology Bombay
Debabrata Maiti: Indian Institute of Technology Bombay

Nature Communications, 2021, vol. 12, issue 1, 1-8

Abstract: Abstract Despite the widespread applications of C–H functionalization, controlling site selectivity remains a significant challenge. Covalently attached directing groups (DGs) served as ancillary ligands to ensure ortho-, 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. Here we report a temporary directing group (TDG) for meta-C–H functionalization via reversible imine formation. By overruling facile ortho-C–H bond activation by imine-N atom, a suitably designed pyrimidine-based TDG successfully delivered selective meta-C–C bond formation. Application of this temporary directing group strategy for streamlining the synthesis of complex organic molecules without any necessary pre-functionalization at the meta position has been explored.

Date: 2021
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DOI: 10.1038/s41467-021-21633-2

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