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  Fluorination of arylboronic esters enabled by bismuth redox catalysis

Planas, O., Wang, F., Leutzsch, M., & Cornella, J. (2020). Fluorination of arylboronic esters enabled by bismuth redox catalysis. Science, 367(6475), 313-317. doi:10.1126/science.aaz2258.

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PlanasWangLeutzschCornella.pdf (Postprint), 2MB
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 Creators:
Planas, Oriol1, Author              
Wang, Feng1, Author              
Leutzsch, Markus2, Author              
Cornella, Josep1, Author              
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1Research Group Cornellà, Max-Planck-Institut für Kohlenforschung, Max Planck Society, ou_2466693              
2Service Department Farès (NMR), Max-Planck-Institut für Kohlenforschung, Max Planck Society, ou_1445623              

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 Abstract: Bismuth catalysis has traditionally relied on the Lewis acidic properties of the element in a fixed oxidation state. In this paper, we report a series of bismuth complexes that can undergo oxidative addition, reductive elimination, and transmetallation in a manner akin to transition metals. Rational ligand optimization featuring a sulfoximine moiety produced an active catalyst for the fluorination of aryl boronic esters through a bismuth (III)/bismuth (V) redox cycle. Crystallographic characterization of the different bismuth species involved, together with a mechanistic investigation of the carbon-fluorine bond-forming event, identified the crucial features that were combined to implement the full catalytic cycle.

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Language(s): eng - English
 Dates: 2020-01-17
 Publication Status: Published in print
 Pages: 5
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 Table of Contents: -
 Rev. Type: Peer
 Identifiers: DOI: 10.1126/science.aaz2258
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Title: Science
  Other : Science
Source Genre: Journal
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Publ. Info: Washington, D.C. : American Association for the Advancement of Science
Pages: - Volume / Issue: 367 (6475) Sequence Number: - Start / End Page: 313 - 317 Identifier: ISSN: 0036-8075
CoNE: https://pure.mpg.de/cone/journals/resource/991042748276600_1