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

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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)

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.

Suggested Citation

  • Kanak Kanti Das & Debasis Aich & Sutapa Dey & Santanu Panda, 2024. "One pot conversion of phenols and anilines to aldehydes and ketones exploiting α gem boryl carbanions," Nature Communications, Nature, vol. 15(1), pages 1-10, December.
    • Handle: RePEc:nat:natcom:v:15:y:2024:i:1:d:10.1038_s41467-024-47156-0
    DOI: 10.1038/s41467-024-47156-0
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    1. Arun Maji & Amit Dahiya & Gang Lu & Trisha Bhattacharya & Massimo Brochetta & Giuseppe Zanoni & Peng Liu & Debabrata Maiti, 2018. "H-bonded reusable template assisted para-selective ketonisation using soft electrophilic vinyl ethers," Nature Communications, Nature, vol. 9(1), pages 1-10, December.
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