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Manganese-Catalyzed C(sp2)-H Borylation of Furan and Thiophene Derivatives

Research output: Contribution to Journal/Magazine › Journal article › peer-review

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Manganese-Catalyzed C(sp2)-H Borylation of Furan and Thiophene Derivatives. / Britton, Luke; Skrodzki, Maciej; Nichol, Gary S. et al.
In: ACS Catalysis, Vol. 11, No. 12, 18.06.2021, p. 6857-6864.

Research output: Contribution to Journal/Magazine › Journal article › peer-review

Harvard

Britton, L, Skrodzki, M, Nichol, GS, Dominey, AP, Pawluć, P, Docherty, JH & Thomas, SP 2021, 'Manganese-Catalyzed C(sp2)-H Borylation of Furan and Thiophene Derivatives', ACS Catalysis, vol. 11, no. 12, pp. 6857-6864. https://doi.org/10.1021/acscatal.1c01563

APA

Britton, L., Skrodzki, M., Nichol, G. S., Dominey, A. P., Pawluć, P., Docherty, J. H., & Thomas, S. P. (2021). Manganese-Catalyzed C(sp2)-H Borylation of Furan and Thiophene Derivatives. ACS Catalysis, 11(12), 6857-6864. https://doi.org/10.1021/acscatal.1c01563

Vancouver

Britton L, Skrodzki M, Nichol GS, Dominey AP, Pawluć P, Docherty JH et al. Manganese-Catalyzed C(sp2)-H Borylation of Furan and Thiophene Derivatives. ACS Catalysis. 2021 Jun 18;11(12):6857-6864. Epub 2021 May 27. doi: 10.1021/acscatal.1c01563

Author

Britton, Luke ; Skrodzki, Maciej ; Nichol, Gary S. et al. / Manganese-Catalyzed C(sp2)-H Borylation of Furan and Thiophene Derivatives. In: ACS Catalysis. 2021 ; Vol. 11, No. 12. pp. 6857-6864.

Bibtex

@article{20f1e3c1676942e7a7405fdf7174557b,
title = "Manganese-Catalyzed C(sp2)-H Borylation of Furan and Thiophene Derivatives",
abstract = "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.",
keywords = "boron, C-H borylation, earth-abundant, manganese, photochemistry",
author = "Luke Britton and Maciej Skrodzki and Nichol, {Gary S.} and Dominey, {Andrew P.} and Piotr Pawlu{\'c} and Docherty, {Jamie H.} and Thomas, {Stephen P.}",
note = "Funding Information: S.P.T. thanks The Royal Society for a University Research Fellowship (RF191015). J.H.D. and S.P.T. acknowledge GSK and EPSRC (PIII0002) and The Royal Society (RF191015) for postdoctoral funding. L.B. acknowledges The Royal Society and The University of Edinburgh for a Ph.D. studentship (RF191015). M.S. acknowledges a Ph.D. studentship grant (POWR.03.02.00-00-I026/16) cofinanced by the European Union through the European Social Fund under the Operational Program Knowledge Education Development. Publisher Copyright: {\textcopyright} ",
year = "2021",
month = jun,
day = "18",
doi = "10.1021/acscatal.1c01563",
language = "English",
volume = "11",
pages = "6857--6864",
journal = "ACS Catalysis",
issn = "2155-5435",
publisher = "American Chemical Society",
number = "12",

}

RIS

TY - JOUR

T1 - Manganese-Catalyzed C(sp2)-H Borylation of Furan and Thiophene Derivatives

AU - Britton, Luke

AU - Skrodzki, Maciej

AU - Nichol, Gary S.

AU - Dominey, Andrew P.

AU - Pawluć, Piotr

AU - Docherty, Jamie H.

AU - Thomas, Stephen P.

N1 - Funding Information: S.P.T. thanks The Royal Society for a University Research Fellowship (RF191015). J.H.D. and S.P.T. acknowledge GSK and EPSRC (PIII0002) and The Royal Society (RF191015) for postdoctoral funding. L.B. acknowledges The Royal Society and The University of Edinburgh for a Ph.D. studentship (RF191015). M.S. acknowledges a Ph.D. studentship grant (POWR.03.02.00-00-I026/16) cofinanced by the European Union through the European Social Fund under the Operational Program Knowledge Education Development. Publisher Copyright: ©

PY - 2021/6/18

Y1 - 2021/6/18

N2 - 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.

AB - 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.

KW - boron

KW - C-H borylation

KW - earth-abundant

KW - manganese

KW - photochemistry

U2 - 10.1021/acscatal.1c01563

DO - 10.1021/acscatal.1c01563

M3 - Journal article

AN - SCOPUS:85108447525

VL - 11

SP - 6857

EP - 6864

JO - ACS Catalysis

JF - ACS Catalysis

SN - 2155-5435

IS - 12

ER -