Ligand Control in Selective C–H Oxidative Functionalization Using Pd-PEPPSI-Type Complexes
(2016) In European Journal of Organic Chemistry 2016(20). p.3395-3400- Abstract
To achieve high selectivity in directed C–H activation, an NHC ligand was introduced to a palladium catalyst. A range of Pd-PEPPSI complexes were applied in the direct acetoxylation of 2-phenylpyridine. The best catalyst was found to be the one based on a diisopropylphenyl-substituted NHC ligand, and this was successfully used for the functionalization of sp2as well as more challenging sp3bonds for a broad variety of substrates. The explored method showed a highly improved selectivity compared to previously reported results with up to 96 % yield for the monoacetoxylated product. Kinetic studies show that sterics of the catalyst is less important in dictating conversion and selectivity; despite an induction period,... (More)
To achieve high selectivity in directed C–H activation, an NHC ligand was introduced to a palladium catalyst. A range of Pd-PEPPSI complexes were applied in the direct acetoxylation of 2-phenylpyridine. The best catalyst was found to be the one based on a diisopropylphenyl-substituted NHC ligand, and this was successfully used for the functionalization of sp2as well as more challenging sp3bonds for a broad variety of substrates. The explored method showed a highly improved selectivity compared to previously reported results with up to 96 % yield for the monoacetoxylated product. Kinetic studies show that sterics of the catalyst is less important in dictating conversion and selectivity; despite an induction period, it was shown that the catalyst is molecular in nature.
(Less)
- author
- Bolbat, Ekaterina LU and Wendt, Ola F. LU
- organization
- publishing date
- 2016
- type
- Contribution to journal
- publication status
- published
- subject
- keywords
- Acetoxylation, C-H activation, NHC ligands, Palladium
- in
- European Journal of Organic Chemistry
- volume
- 2016
- issue
- 20
- pages
- 6 pages
- publisher
- John Wiley & Sons Inc.
- external identifiers
-
- scopus:84978715268
- wos:000380138100019
- ISSN
- 1434-193X
- DOI
- 10.1002/ejoc.201600322
- language
- English
- LU publication?
- yes
- id
- 36b69638-67e3-4557-8fc9-5c8751144e8d
- date added to LUP
- 2017-01-16 15:28:44
- date last changed
- 2024-01-04 20:49:45
@article{36b69638-67e3-4557-8fc9-5c8751144e8d,
abstract = {{<p>To achieve high selectivity in directed C–H activation, an NHC ligand was introduced to a palladium catalyst. A range of Pd-PEPPSI complexes were applied in the direct acetoxylation of 2-phenylpyridine. The best catalyst was found to be the one based on a diisopropylphenyl-substituted NHC ligand, and this was successfully used for the functionalization of sp<sup>2</sup>as well as more challenging sp<sup>3</sup>bonds for a broad variety of substrates. The explored method showed a highly improved selectivity compared to previously reported results with up to 96 % yield for the monoacetoxylated product. Kinetic studies show that sterics of the catalyst is less important in dictating conversion and selectivity; despite an induction period, it was shown that the catalyst is molecular in nature.</p>}},
author = {{Bolbat, Ekaterina and Wendt, Ola F.}},
issn = {{1434-193X}},
keywords = {{Acetoxylation; C-H activation; NHC ligands; Palladium}},
language = {{eng}},
number = {{20}},
pages = {{3395--3400}},
publisher = {{John Wiley & Sons Inc.}},
series = {{European Journal of Organic Chemistry}},
title = {{Ligand Control in Selective C–H Oxidative Functionalization Using Pd-PEPPSI-Type Complexes}},
url = {{http://dx.doi.org/10.1002/ejoc.201600322}},
doi = {{10.1002/ejoc.201600322}},
volume = {{2016}},
year = {{2016}},
}