Copper-NHC-Mediated Semi-Hydrogenation and Hydroboration of Alkynes: Enhanced Catalytic Activity Using Ring-Expanded Carbenes

Jonathan Hall; Darcy Unson; Paul Brunel; Lee Collins; Mateusz Cybulski; Mary Mahon; Michael Whittlesey

doi:10.1021/acs.organomet.8b00467

Copper-NHC-Mediated Semi-Hydrogenation and Hydroboration of Alkynes: Enhanced Catalytic Activity Using Ring-Expanded Carbenes

Jonathan Hall
, Darcy Unson
, Paul Brunel
, Lee Collins
, Mateusz Cybulski
, Mary Mahon
, Michael Whittlesey

Department of Chemistry

Research output: Contribution to journal › Article › peer-review

65 Citations (SciVal)

346 Downloads (Pure)

Abstract

A series of two-coordinate copper tert-butoxide complexes bearing five-, six-, and seven-membered ring N-heterocyclic carbenes, prepared by protonolysis of (NHC)CuMes with tBuOH, have been used as catalytic precursors in the semihydrogenation of alkynes with silanes/tBuOH and the hydroboration of alkynes with HBPin. Both processes proceed with high regioselectivity and show enhancements with six- and seven-membered ring carbenes.

Original language	English
Pages (from-to)	3102-3110
Number of pages	9
Journal	Organometallics
Volume	37
Issue number	18
Early online date	31 Aug 2018
DOIs	https://doi.org/10.1021/acs.organomet.8b00467
Publication status	Published - 24 Sept 2018

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10.1021/acs.organomet.8b00467

Whittlesey_revised_manuscript.PDF
This document is the Accepted Manuscript version of a Published Work that appeared in final form in Organometallics, copyright © American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see: https://dx.doi.org/10.1021/acs.organomet.8b00467
Accepted author manuscript, 1.22 MB

Avance NEO 500 MHz Nuclear Magnetic Resonance (NMR) Spectrometer (1South)
Material and Chemical Characterisation (MC2)
Facility/equipment: Equipment
Dual source (Cu and Mo) Single Crystal Diffractometer (SuperNova)
Material and Chemical Characterisation (MC2)
Facility/equipment: Equipment
Propulse 500 MHz Nuclear Magnetic Resonance (NMR) Spectrometer (1South)
Material and Chemical Characterisation (MC2)
Facility/equipment: Equipment

Cite this

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title = "Copper-NHC-Mediated Semi-Hydrogenation and Hydroboration of Alkynes: Enhanced Catalytic Activity Using Ring-Expanded Carbenes",

abstract = "A series of two-coordinate copper tert-butoxide complexes bearing five-, six-, and seven-membered ring N-heterocyclic carbenes, prepared by protonolysis of (NHC)CuMes with tBuOH, have been used as catalytic precursors in the semihydrogenation of alkynes with silanes/tBuOH and the hydroboration of alkynes with HBPin. Both processes proceed with high regioselectivity and show enhancements with six- and seven-membered ring carbenes.",

author = "Jonathan Hall and Darcy Unson and Paul Brunel and Lee Collins and Mateusz Cybulski and Mary Mahon and Michael Whittlesey",

year = "2018",

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doi = "10.1021/acs.organomet.8b00467",

language = "English",

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T1 - Copper-NHC-Mediated Semi-Hydrogenation and Hydroboration of Alkynes: Enhanced Catalytic Activity Using Ring-Expanded Carbenes

AU - Hall, Jonathan

AU - Unson, Darcy

AU - Brunel, Paul

AU - Collins, Lee

AU - Cybulski, Mateusz

AU - Mahon, Mary

AU - Whittlesey, Michael

PY - 2018/9/24

Y1 - 2018/9/24

N2 - A series of two-coordinate copper tert-butoxide complexes bearing five-, six-, and seven-membered ring N-heterocyclic carbenes, prepared by protonolysis of (NHC)CuMes with tBuOH, have been used as catalytic precursors in the semihydrogenation of alkynes with silanes/tBuOH and the hydroboration of alkynes with HBPin. Both processes proceed with high regioselectivity and show enhancements with six- and seven-membered ring carbenes.

AB - A series of two-coordinate copper tert-butoxide complexes bearing five-, six-, and seven-membered ring N-heterocyclic carbenes, prepared by protonolysis of (NHC)CuMes with tBuOH, have been used as catalytic precursors in the semihydrogenation of alkynes with silanes/tBuOH and the hydroboration of alkynes with HBPin. Both processes proceed with high regioselectivity and show enhancements with six- and seven-membered ring carbenes.

U2 - 10.1021/acs.organomet.8b00467

DO - 10.1021/acs.organomet.8b00467

M3 - Article

SN - 0276-7333

VL - 37

SP - 3102

EP - 3110

JO - Organometallics

JF - Organometallics

IS - 18

ER -

Copper-NHC-Mediated Semi-Hydrogenation and Hydroboration of Alkynes: Enhanced Catalytic Activity Using Ring-Expanded Carbenes

Abstract

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Equipment

Avance NEO 500 MHz Nuclear Magnetic Resonance (NMR) Spectrometer (1South)

Dual source (Cu and Mo) Single Crystal Diffractometer (SuperNova)

Propulse 500 MHz Nuclear Magnetic Resonance (NMR) Spectrometer (1South)

Cite this