Synthesis 2023; 55(19): 3113-3120
DOI: 10.1055/a-2096-6841
paper

Synthesis of N-Phenylcarbamate by C–N Coupling Reaction without Metal Participation

Long Ji
,

The National Natural Science Foundation of China (Grant No. 21961038), and the Shanghai Cooperation Organization Science and Technology Partnership Program (No. 2022E01049).


Abstract

We have developed a new method for the synthesis of carbamates from amine and hydrazine formate. The reaction occurs in the presence of iodine and tert-butyl hydroperoxide, in which carbazates are produced via alkoxycarbonyl radical formation for cross-coupling reaction. The method exhibits broad functional group tolerance and affords a series of N-phenylcarbamates in moderate to good yields. Remarkably, our approach is metal free and utilizes cheap, readily available raw materials and relatively universal substrates.

Supporting Information



Publication History

Received: 02 April 2023

Accepted after revision: 22 May 2023

Accepted Manuscript online:
22 May 2023

Article published online:
27 June 2023

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