DMAP Catalyzed One-Pot Curtius Rearrangement Using 1,1-Dimethyl-2,2,2-trichloroethoxycarbonyl Azide

Ken Lin and Hongjian Lu*

*Institute of Chemistry and BioMedical Sciences, School of Chemistry and Chemical Engineering, Nanjing University, Nanjing 210093, China, Email: hongjianlunju.edu.cn

K. Lin, H. Lu, Org. Lett., 2023, 25, 4534-4539.

DOI: 10.1021/acs.orglett.3c01580

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Abstract

DMAP catalyzes a controllable, base-free, decarboxylative isocyanation of carboxylic acids with 1,1-dimethyl-2,2,2-trichloroethoxycarbonyl azide (DMTN₃). The scope of this one-pot Curtius rearrangement covers a range of primary, secondary, and tertiary alkyl and aryl carboxylic acids. Examples are reported of late-stage modifications of natural products and drug molecules.

see article for more examples

proposed mechanism

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Key Words

Curtius rearrangement, isocyanation

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ID: J54-Y2023