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@article{Higham:2022:10.1002/anie.202202933,
author = {Higham, J and Bull, J},
doi = {10.1002/anie.202202933},
journal = {Angewandte Chemie International Edition},
pages = {1--8},
title = {Amine-catalyzed copper-mediated C–H sulfonylation of benzaldehydes via a transient imine directing group},
url = {http://dx.doi.org/10.1002/anie.202202933},
volume = {61},
year = {2022}
}

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TY  - JOUR
AB  - Transient directing groups (TDGs) can provide a powerful means for C–H functionalization without requiring additional steps for directing group introduction and removal. We report the first use of a TDG in combination with copper to effect C–H functionalization. The regioselective copper mediated beta–C(sp2)–H sulfonylation of aldehydes with sulfinate salts is accomplished using catalytic β-alanine to form a transient imine. A broad range of sulfonylated benzaldehydes are prepared using copper fluoride as both copper source and oxidant, involving a [5,6] cupracyclic intermediate. gamma-(peri)-Sulfonylation of napthyl and phenanthrenyl carboxaldehydes is achieved through [6,6] cupracyclic intermediates. Further derivatisation of the aldehyde products is demonstrated. Kinetic experiments and Hammett analysis suggest the turnover limiting step to be a concerted asynchronous C–H cleavage via a dearomative Wheland-type transition state.
AU  - Higham,J
AU  - Bull,J
DO  - 10.1002/anie.202202933
EP  - 8
PY  - 2022///
SN  - 1433-7851
SP  - 1
TI  - Amine-catalyzed copper-mediated C–H sulfonylation of benzaldehydes via a transient imine directing group
T2  - Angewandte Chemie International Edition
UR  - http://dx.doi.org/10.1002/anie.202202933
UR  - https://doi.org/10.1002/anie.202202933
UR  - http://hdl.handle.net/10044/1/97087
VL  - 61
ER  -

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Dr James A Bull

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