Journal of the American Chemical Society, volume 137, issue 22, pages 7224-7230
An Umpolung Approach to Alkene Carboamination: Palladium Catalyzed 1,2-Amino-Acylation, -Carboxylation, -Arylation, -Vinylation, and -Alkynylation
2
AstraZeneca, Alderley Park, Macclesfield, Cheshire SK10 4TG, United Kingdom
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Publication type: Journal Article
Publication date: 2015-05-28
Quartile SCImago
Q1
Quartile WOS
Q1
Impact factor: 15
ISSN: 00027863, 15205126
General Chemistry
Catalysis
Biochemistry
Colloid and Surface Chemistry
Abstract
Conventional approaches to Pd-catalyzed alkene 1,2-carboamination rely upon the combination of a nucleophilic nitrogen-based component and an internal C-based or external oxidant. In this study, we outline an umpolung approach, which is triggered by oxidative initiation at an electrophilic N-based component and employs "standard" organometallic nucleophiles to introduce the new carbon-based fragment. Specifically, oxidative addition of a Pd(0)-catalyst into the N-O bond of O-pentafluorobenzoyl oxime esters generates imino-Pd(II) intermediates, which undergo 5-exo cyclization with sterically diverse alkenes. The resultant alkyl-Pd(II) intermediates are intercepted by organometallic nucleophiles or alcohols, under carbonylative or noncarbonylative conditions, to provide 1,2-carboamination products. This approach provides, for the first time, a unified strategy for achieving alkene 1,2-amino-acylation, -carboxylation, -arylation, -vinylation, and -alkynylation. For carbonylative processes, orchestrated protodecarboxylation of the pentafluorobenzoate leaving group underpins reaction efficiency. This process is likely a key feature in related Narasaka-Heck cyclizations and accounts for the efficacy of O-pentafluorobenzoyl oxime esters in aza-Heck reactions of this type.
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10
20
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- We do not take into account publications without a DOI.
- Statistics recalculated only for publications connected to researchers, organizations and labs registered on the platform.
- Statistics recalculated weekly.
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Faulkner A., Scott J., Bower J. E. An Umpolung Approach to Alkene Carboamination: Palladium Catalyzed 1,2-Amino-Acylation, -Carboxylation, -Arylation, -Vinylation, and -Alkynylation // Journal of the American Chemical Society. 2015. Vol. 137. No. 22. pp. 7224-7230.
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Faulkner A., Scott J., Bower J. E. An Umpolung Approach to Alkene Carboamination: Palladium Catalyzed 1,2-Amino-Acylation, -Carboxylation, -Arylation, -Vinylation, and -Alkynylation // Journal of the American Chemical Society. 2015. Vol. 137. No. 22. pp. 7224-7230.
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TY - JOUR
DO - 10.1021/jacs.5b03732
UR - https://doi.org/10.1021/jacs.5b03732
TI - An Umpolung Approach to Alkene Carboamination: Palladium Catalyzed 1,2-Amino-Acylation, -Carboxylation, -Arylation, -Vinylation, and -Alkynylation
T2 - Journal of the American Chemical Society
AU - Faulkner, Adele
AU - Scott, J
AU - Bower, John Eric
PY - 2015
DA - 2015/05/28 00:00:00
PB - American Chemical Society (ACS)
SP - 7224-7230
IS - 22
VL - 137
SN - 0002-7863
SN - 1520-5126
ER -
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@article{2015_Faulkner,
author = {Adele Faulkner and J Scott and John Eric Bower},
title = {An Umpolung Approach to Alkene Carboamination: Palladium Catalyzed 1,2-Amino-Acylation, -Carboxylation, -Arylation, -Vinylation, and -Alkynylation},
journal = {Journal of the American Chemical Society},
year = {2015},
volume = {137},
publisher = {American Chemical Society (ACS)},
month = {may},
url = {https://doi.org/10.1021/jacs.5b03732},
number = {22},
pages = {7224--7230},
doi = {10.1021/jacs.5b03732}
}
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Faulkner, Adele, et al. “An Umpolung Approach to Alkene Carboamination: Palladium Catalyzed 1,2-Amino-Acylation, -Carboxylation, -Arylation, -Vinylation, and -Alkynylation.” Journal of the American Chemical Society, vol. 137, no. 22, May. 2015, pp. 7224-7230. https://doi.org/10.1021/jacs.5b03732.