Taming Brønsted acid reactivity: nucleophilic substitutions of propargylic alcohols with n-nucleophiles mediated by phosphorus-based Brønsted acid catalysts
File(s)acsomega.9b01427.pdf (1.05 MB)
Published version
Author(s)
Radtanajiravong, Lalita
Diez-Gonzalez, Silvia
Type
Journal Article
Abstract
The activity of diethyl phosphite and diphenyl phosphate in propargylation reactions
with N-nucleophiles of varying basicity is presented. Careful choice of the reaction conditions
minimised undesired rearrangements and arylation processes, typical side reactions with
Brønsted acid catalysis. These systems are compatible with technical solvents and presence of
air and they are also applicable to C-, O- and S-nucleophiles
with N-nucleophiles of varying basicity is presented. Careful choice of the reaction conditions
minimised undesired rearrangements and arylation processes, typical side reactions with
Brønsted acid catalysis. These systems are compatible with technical solvents and presence of
air and they are also applicable to C-, O- and S-nucleophiles
Date Issued
2019-07-31
Date Acceptance
2019-06-14
Citation
ACS Omega, 2019, 4 (7), pp.12300-12307
ISSN
2470-1343
Publisher
American Chemical Society
Start Page
12300
End Page
12307
Journal / Book Title
ACS Omega
Volume
4
Issue
7
Copyright Statement
© 2019 American Chemical Society. This is an open access article published under a Creative Commons Attribution (CC-BY)
License (http://pubs.acs.org/page/policy/authorchoice_ccby_termsofuse.html), which permits unrestricted use, distribution and reproduction in any medium,
provided the author and source are cited.
License (http://pubs.acs.org/page/policy/authorchoice_ccby_termsofuse.html), which permits unrestricted use, distribution and reproduction in any medium,
provided the author and source are cited.
Subjects
Science & Technology
Physical Sciences
Chemistry, Multidisciplinary
Chemistry
CHEMISTRY RESEARCH AREAS
ONE-POT SYNTHESIS
METAL-FREE
HIGHLY EFFICIENT
HYDROLYSIS
PERSPECTIVE
ALKYLATION
MECHANISMS
PHOSPHITES
INDOLES
Publication Status
Published
Date Publish Online
2019-07-18