Issue 35, 2019, Issue in Progress

Quick construction of a C–N bond from arylsulfonyl hydrazides and Csp2–X compounds promoted by DMAP at room temperature

Abstract

An efficient approach for C–N bond construction by the coupling reaction of arylsulfonyl hydrazides and Csp2–X compounds is described for the first time with good yields at room temperature. The reaction promoted by the simple base DMAP displays excellent regioselectivity as well as high functional group tolerance with 41 examples. Even for inactive Csp2–Cl compounds, the metal-free transformation also affords a satisfactory yield after prolonging the reaction time, which is comparable to that of the corresponding Csp2–Br compound. The good effect of DMAP and its action mechanism are confirmed by the competitive experiments of reactivity between Cl-substituted and Br-substituted substrates and the single-crystal X-ray analysis of the key intermediate quaternary ammonium salt. Importantly, the application of this method for a gram-scale (even over 10 g) preparation can be accomplished.

Graphical abstract: Quick construction of a C–N bond from arylsulfonyl hydrazides and Csp2–X compounds promoted by DMAP at room temperature

Supplementary files

Article information

Article type
Paper
Submitted
06 May 2019
Accepted
17 Jun 2019
First published
26 Jun 2019
This article is Open Access
Creative Commons BY-NC license

RSC Adv., 2019,9, 19917-19923

Quick construction of a C–N bond from arylsulfonyl hydrazides and Csp2–X compounds promoted by DMAP at room temperature

K. Yang, J. Gao, S. Luo, H. Wu, C. Pang, B. Wang, X. Chen and Z. Wang, RSC Adv., 2019, 9, 19917 DOI: 10.1039/C9RA03403J

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