Regioselective ortho halogenation of N -aryl amides and ureas via oxidative halodeboronation: harnessing boron reactivity for efficient C-halogen bond installation.

Autor:	Shinde GH; Department of Chemistry and Molecular Biology, University of Gothenburg SE-41296 Gothenburg Sweden henrik.sunden@chem.gu.se., Ghotekar GS; Department of Chemistry and Molecular Biology, University of Gothenburg SE-41296 Gothenburg Sweden henrik.sunden@chem.gu.se., Amombo Noa FM; Department of Chemistry and Chemical Engineering, Chalmers University of Technology SE-41296 Gothenburg Sweden., Öhrström L; Department of Chemistry and Chemical Engineering, Chalmers University of Technology SE-41296 Gothenburg Sweden., Norrby PO; Data Science and Modelling, Pharmaceutical Sciences, R&D, AstraZeneca Gothenburg Pepparedsleden 1 Mölndal SE-43183 Sweden., Sundén H; Department of Chemistry and Molecular Biology, University of Gothenburg SE-41296 Gothenburg Sweden henrik.sunden@chem.gu.se.; Department of Chemistry and Chemical Engineering, Chalmers University of Technology SE-41296 Gothenburg Sweden.
Jazyk:	angličtina
Zdroj:	Chemical science [Chem Sci] 2023 Oct 23; Vol. 14 (46), pp. 13429-13436. Date of Electronic Publication: 2023 Oct 23 (Print Publication: 2023).
DOI:	10.1039/d3sc04628a
Abstrakt:	The installation of the C-halogen bond at the ortho position of N -aryl amides and ureas represents a tool to prepare motifs that are ubiquitous in biologically active compounds. To construct such prevalent bonds, most methods require the use of precious metals and a multistep process. Here we report a novel protocol for the long-standing challenge of regioselective ortho halogenation of N -aryl amides and ureas using an oxidative halodeboronation. By harnessing the reactivity of boron over nitrogen, we merge carbonyl-directed borylation with consecutive halodeboronation, enabling the precise introduction of the C-X bond at the desired ortho position of N -aryl amides and ureas. This method offers an efficient, practical, and scalable solution for synthesizing halogenated N -heteroarenes under mild conditions, highlighting the superiority of boron reactivity in directing the regioselectivity of the reaction. Competing Interests: The authors declare no conflict of interest. (This journal is © The Royal Society of Chemistry.)
Databáze:	MEDLINE
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