One pot conversion of phenols and anilines to aldehydes and ketones exploiting α gem boryl carbanions

Kanak Kanti Das, Debasis Aich, Sutapa Dey and Santanu Panda ()
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Kanak Kanti Das: Indian Institute of Technology Kharagpur
Debasis Aich: Indian Institute of Technology Kharagpur
Sutapa Dey: Indian Institute of Technology Kharagpur
Santanu Panda: Indian Institute of Technology Kharagpur

Nature Communications, 2024, vol. 15, issue 1, 1-10

Abstract: Abstract Functional group interconversion is an important asset in organic synthesis. Phenols/anilines being naturally abundant and the carbonyl being the most common in a wide range of bioactive molecules, an efficient conversion is of prime interest. The reported methods require transition metal catalyzed cross coupling which limits its applicability. Here we have described a method for synthesizing various aldehydes and ketones, starting from phenol and protected anilines via Csp2-O/N bond cleavage in a one-pot/stepwise manner. Our synthetic method is found to be compatible with a diverse range of phenols and anilines carrying sensitive functional groups including halides, esters, ketal, hydroxyl, alkenes, and terminal alkynes as well as the substitution on the aryl cores. A short-step synthesis of bioactive molecules and their functionalization have been executed. Starting from BINOL, a photocatalyst has been designed. Here, we have developed a transition metal-free protocol for the conversion of phenols and anilines to aldehydes and ketones.

Date: 2024
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DOI: 10.1038/s41467-024-47156-0

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