Iron-catalysed substrate-directed Suzuki biaryl cross-coupling

Harry M. O'Brien; Mattia Manzotti; Roman D. Abrams; David Elorriaga; Hazel A. Sparkes; Sean A. Davis; Robin B. Bedford

doi:10.1038/s41929-018-0081-x

Iron-catalysed substrate-directed Suzuki biaryl cross-coupling

Harry M. O'Brien, Mattia Manzotti, Roman D. Abrams, David Elorriaga, Hazel A. Sparkes, Sean A. Davis, Robin B. Bedford^*

^*Corresponding author for this work

Research output: Contribution to journal › Article (Academic Journal)

36 Citations (Scopus)

366 Downloads (Pure)

Abstract

Although the replacement of ubiquitous palladium catalysts with more sustainable iron-based analogues continues apace, the simple biaryl Suzuki cross-coupling reaction remains stubbornly elusive. It appears that the main issue hampering the reaction is activation of the aryl halide C-X bond. Here we show that a simple N-pyrrole amide and related directing groups on the aryl halide substrates facilitate this process by transient π-coordination to the iron centre. This allows iron-catalysed Suzuki biaryl cross-coupling to proceed, under mild conditions, with alkyllithium-activated aryl pinacol boronic esters.

Original language	English
Pages (from-to)	429-437
Number of pages	9
Journal	Nature Catalysis
Volume	1
Issue number	6
Early online date	12 Jun 2018
DOIs	https://doi.org/10.1038/s41929-018-0081-x
Publication status	Published - Jun 2018

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10.1038/s41929-018-0081-x

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Iron-Catalysed Suzuki Nature Catalysis 2018
Bedford, R. B. (Creator), O'Brien, H. (Creator), Manzotti, M. (Creator) & Davis, S. A. (Creator), University of Bristol, 24 May 2018
DOI: 10.5523/bris.1egk09qs16sej2ru76yju7q572, http://data.bris.ac.uk/data/dataset/1egk09qs16sej2ru76yju7q572
Dataset

Professor Robin B Bedford
- R.Bedford@bristol.ac.uk
- School of Chemistry - Professor of Catalysis
- Synthesis
- Supramolecular and Mechanistic Chemistry
- Catalysis
Person: Academic , Member
Dr Sean A Davis
- S.A.Davis@bristol.ac.uk
- The Bristol Centre for Nanoscience and Quantum Information
- School of Chemistry - Senior Lecturer
- Soft Matter, Colloids and Materials
Person: Academic , Member

Cite this

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title = "Iron-catalysed substrate-directed Suzuki biaryl cross-coupling",

abstract = "Although the replacement of ubiquitous palladium catalysts with more sustainable iron-based analogues continues apace, the simple biaryl Suzuki cross-coupling reaction remains stubbornly elusive. It appears that the main issue hampering the reaction is activation of the aryl halide C-X bond. Here we show that a simple N-pyrrole amide and related directing groups on the aryl halide substrates facilitate this process by transient π-coordination to the iron centre. This allows iron-catalysed Suzuki biaryl cross-coupling to proceed, under mild conditions, with alkyllithium-activated aryl pinacol boronic esters.",

author = "O'Brien, {Harry M.} and Mattia Manzotti and Abrams, {Roman D.} and David Elorriaga and Sparkes, {Hazel A.} and Davis, {Sean A.} and Bedford, {Robin B.}",

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doi = "10.1038/s41929-018-0081-x",

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T1 - Iron-catalysed substrate-directed Suzuki biaryl cross-coupling

AU - O'Brien, Harry M.

AU - Manzotti, Mattia

AU - Abrams, Roman D.

AU - Elorriaga, David

AU - Sparkes, Hazel A.

AU - Davis, Sean A.

AU - Bedford, Robin B.

PY - 2018/6

Y1 - 2018/6

N2 - Although the replacement of ubiquitous palladium catalysts with more sustainable iron-based analogues continues apace, the simple biaryl Suzuki cross-coupling reaction remains stubbornly elusive. It appears that the main issue hampering the reaction is activation of the aryl halide C-X bond. Here we show that a simple N-pyrrole amide and related directing groups on the aryl halide substrates facilitate this process by transient π-coordination to the iron centre. This allows iron-catalysed Suzuki biaryl cross-coupling to proceed, under mild conditions, with alkyllithium-activated aryl pinacol boronic esters.

AB - Although the replacement of ubiquitous palladium catalysts with more sustainable iron-based analogues continues apace, the simple biaryl Suzuki cross-coupling reaction remains stubbornly elusive. It appears that the main issue hampering the reaction is activation of the aryl halide C-X bond. Here we show that a simple N-pyrrole amide and related directing groups on the aryl halide substrates facilitate this process by transient π-coordination to the iron centre. This allows iron-catalysed Suzuki biaryl cross-coupling to proceed, under mild conditions, with alkyllithium-activated aryl pinacol boronic esters.

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JF - Nature Catalysis

SN - 2520-1158

IS - 6

ER -

Iron-catalysed substrate-directed Suzuki biaryl cross-coupling

Abstract

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Iron-Catalysed Suzuki Nature Catalysis 2018

Professor Robin B Bedford

Dr Sean A Davis

Cite this