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

ABSTRACT: In nature, enzymatic pathways generate C_aryl-C(O) bonds in a site-selective fashion. Synthetically, C_aryl-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. S

SUBMITTER: Maji A 

PROVIDER: S-EPMC6123475 | biostudies-literature | 2018 Sep

REPOSITORIES: biostudies-literature