In this section
@article{Braddock:2023:10.1021/acs.joc.3c00585,
author = {Braddock, D and Rowley, B and Lickiss, P and Fussell, S and Qamar, R and Pugh, D and Rzepa, H and White, A},
doi = {10.1021/acs.joc.3c00585},
journal = {Journal of Organic Chemistry},
pages = {9853--9869},
title = {On the use of triarylsilanols as catalysts for direct amidation of carboxylic acids},
url = {http://dx.doi.org/10.1021/acs.joc.3c00585},
volume = {88},
year = {2023}
}
TY - JOUR
AB - Triarylsilanols are reported as the first silicon-centred molecular catalysts for direct amidation of carboxylic acids with amines as identified after a screen of silanols, silanediols, disiloxanediols and incompletely condensed silsesquioxanes as potential homogeneous catalysts. Subsequent synthesis and testing of various electronically differentiated triarylsilanols identify tris(p-haloaryl)silanols as more active than the parent triarylsilanol, where the bromide congener was found to be the most active. Catalyst decomposition can be observed by NMR methods, but RPKA methods reveal that product inhibition is operative, where tertiary amides are more inhibitory than secondary amides. Studies using an authentically synthesised triaryl silylester as a putative intermediate in the catalytic system enable a plausible mechanism to be proposed as supported by computations.
AU - Braddock,D
AU - Rowley,B
AU - Lickiss,P
AU - Fussell,S
AU - Qamar,R
AU - Pugh,D
AU - Rzepa,H
AU - White,A
DO - 10.1021/acs.joc.3c00585
EP - 9869
PY - 2023///
SN - 0022-3263
SP - 9853
TI - On the use of triarylsilanols as catalysts for direct amidation of carboxylic acids
T2 - Journal of Organic Chemistry
UR - http://dx.doi.org/10.1021/acs.joc.3c00585
UR - https://pubs.acs.org/doi/10.1021/acs.joc.3c00585
UR - http://hdl.handle.net/10044/1/105027
VL - 88
ER -