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DOI: 10.1055/a-2202-2263
Carboxamide-Accelerated Chemoselective Borylation of Iodoarenes under Photoirradiation
We warmly thank Yamaguchi University, the Japan Science and Technology Agency (JST) SPRING Grant Number JPMJSP2111, Japan Society for the Promotion of Science (JSPS) Grants-in-Aid for Scientific Research (B) Grant Number 21H01939, JST CREST (JPMJCR18R4), and JST ASTEP (JPMJTM22DY). This work was also the result of using research equipment shared in a Ministry of Education, Culture, Sports, Science and Technology (MEXT) Project for promoting public utilization of advanced research infrastructure (Program for supporting construction of core facilities) Grant Number JPMXS0440400023.
Dedicated to Prof. Dennis Curran on the occasion of his 70th birthday.
Abstract
Borylation of haloarenes is one of the most important methodologies to synthesize borylated arenes. Generally, borylation of haloarenes occurs smoothly at the sterically less hindered para or meta position by the use of a transition metal catalyst or a photoredox catalyst or under basic conditions. This study reports on the ortho-specific and chemoselective borylation of ortho-iodoarene possessing carboxamide under visible-light irradiation. When a haloarene containing both C–I and C–X bonds is employed as a substrate, another C–X bond (not ortho) remains intact during the reaction. Mechanistic studies revealed that the key to the success of this reaction is the generation of a diboron-bridged five-membered ring as a transition state, in which the diboron-bridged five-membered ring and the benzene ring in the transition state are perpendicular to each other, owing to steric repulsion by the iodine atom at the ortho position. This chemoselectivity is suitable for the synthesis of borylated building blocks.
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-2202-2263.
- Supporting Information
Publikationsverlauf
Eingereicht: 06. Oktober 2023
Angenommen nach Revision: 31. Oktober 2023
Accepted Manuscript online:
31. Oktober 2023
Artikel online veröffentlicht:
30. November 2023
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For recent reviews, see:
For other recent borylations, see:
For other chemoselective cross-couplings, see: