H-bonded reusable template assisted para-selective ketonisation using soft electrophilic vinyl ethers

Arun Maji, Amit Dahiya, Gang Lu, Trisha Bhattacharya, Massimo Brochetta, Giuseppe Zanoni (), Peng Liu () and Debabrata Maiti ()
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Arun Maji: Indian Institute of Technology Bombay
Amit Dahiya: Indian Institute of Technology Bombay
Gang Lu: University of Pittsburgh
Trisha Bhattacharya: Indian Institute of Technology Bombay
Massimo Brochetta: Università degli Studi di Pavia
Giuseppe Zanoni: Università degli Studi di Pavia
Peng Liu: University of Pittsburgh
Debabrata Maiti: Indian Institute of Technology Bombay

Nature Communications, 2018, vol. 9, issue 1, 1-10

Abstract: Abstract In nature, enzymatic pathways generate Caryl−C(O) bonds in a site-selective fashion. Synthetically, Caryl−C(O) bonds are synthesised in organometallic reactions using prefunctionalized substrate materials. Electrophilic routes are largely limited to electron-rich systems, non-polar medium, and multiple product formations with a limited scope of general application. Herein we disclose a directed para-selective ketonisation technique of arenes, overriding electronic bias and structural congestion, in the presence of a polar protic solvent. The concept of hard–soft interaction along with in situ activation techniques is utilised to suppress the competitive routes. Mechanistic pathways are investigated both experimentally and computationally to establish the hypothesis. Synthetic utility of the protocol is highlighted in formal synthesis of drugs, drug cores, and bioactive molecules.

Date: 2018
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DOI: 10.1038/s41467-018-06018-2

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