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Manganese-Catalyzed C(sp2)–H Borylation of Furan and Thiophene Derivatives
Authors:
- Luke Britton,
- Maciej Skrodzki,
- Gary S. Nichol,
- Andrew P. Dominey,
- Piotr Pawluć,
- Jamie H. Docherty,
- Stephen P. Thomas
- Record ID
- UAM008af396880a44a18e249aed7af0cbf1
- Author
- Journal series
- ACS Catalysis, ISSN 2155-5435
- Issue year
- 2021
- Vol
- 11
- No
- 12
- Pages
- 6857-6864
- Keywords in original language
- manganese earth-abundant C−H borylation boron photochemistry
- ASJC Classification
- Abstract in original language
- Aryl boronic esters are bench-stable, platform building-blocks that can be accessed through metal-catalyzed aryl C(sp2)–H borylation reactions. C(sp2)–H bond functionalization reactions using rare- and precious-metal catalysts are well established, and while examples utilizing Earth-abundant alternatives have emerged, manganese catalysis remains lacking. The manganese-catalyzed C–H borylation of furan and thiophene derivatives is reported alongside an in situ activation method providing facile access to the active manganese hydride species. Mechanistic investigations showed that blue light irradiation directly affected catalysis by action at the metal center, that C(sp2)–H bond borylation occurs through a C–H metallation pathway, and that the reversible coordination of pinacolborane to the catalyst gave a manganese borohydride complex, which was as an off-cycle resting state.
- DOI
- DOI:10.1021/acscatal.1c01563 Opening in a new tab
- URL
- https://pubs.acs.org/doi/10.1021/acscatal.1c01563 Opening in a new tab
- Language
- eng (en) English
- Score (nominal)
- 200
- Score source
- journalList
- Score
- = 200.0, 15-05-2022, ArticleFromJournal
- Publication indicators
- = 1; : 2018 = 2.116; : 2019 (2 years) = 12.350 - 2019 (5 years) =12.741
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- Uniform Resource Identifier
- https://researchportal.amu.edu.pl/info/article/UAM008af396880a44a18e249aed7af0cbf1/
- URN
urn:amu-prod:UAM008af396880a44a18e249aed7af0cbf1
* presented citation count is obtained through Internet information analysis and it is close to the number calculated by the Publish or PerishOpening in a new tab system.