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 Electrophilic acylation of arenes is largely limited to electron rich systems, non-polar medium and often displays moderate selectivity Here, the authors show a directed para-selective ketonisation of arenes, overriding electronic bias and structural congestion, and apply it to the synthesis of bioactive compounds

/pdf/h-bonded-reusable-template-assisted-para-selective-2vex6s15pw.pdf

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

Hydroxyl-Assisted Carbonylation of Alkenyltin Derivatives: Development and Application to a Formal Synthesis of Tubelactomicin A.

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Hydroxyl-Assisted Carbonylation of Alkenyltin Derivatives: Development and Application to a Formal Synthesis of Tubelactomicin A.