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Article: A Hydrazone-Based exo-Directing-Group Strategy for β C-H Oxidation of Aliphatic Amines

TitleA Hydrazone-Based exo-Directing-Group Strategy for β C-H Oxidation of Aliphatic Amines
Authors
KeywordsPalladium
Amines
C-H activation
Hydrazones
Oxidation
Issue Date2016
Citation
Angewandte Chemie - International Edition, 2016, v. 55, n. 17, p. 5299-5303 How to Cite?
Abstract© 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim. Described is a new hydrazone-based exo-directing group (DG) strategy developed for the functionalization of unactivated primary β C-H bonds of aliphatic amines. Conveniently synthesized from protected primary amines, the hydrazone DGs are shown to site-selectively promote the β-acetoxylation and tosyloxylation via five-membered exo-palladacycles. Amines with a wide scope of skeletons and functional groups are tolerated. Moreover, the hydrazone DG can be readily removed, and a one-pot C-H acetoxylation/DG removal protocol was also discovered. All about the DGs: A hydrazone-based exo-directing group (DG) strategy is developed for the functionalization of unactivated primary β C-H bonds of aliphatic amines. The hydrazone DGs can be conveniently installed and removed, and promote β-acetoxylation and tosyloxylation via a five-membered exo-palladacycle. PG=protecting group, Ts=4-toluenesulfonyl.
Persistent Identifierhttp://hdl.handle.net/10722/276503
ISSN
2017 Impact Factor: 12.102
2015 SCImago Journal Rankings: 6.229
ISI Accession Number ID

 

DC FieldValueLanguage
dc.contributor.authorHuang, Zhongxing-
dc.contributor.authorWang, Chengpeng-
dc.contributor.authorDong, Guangbin-
dc.date.accessioned2019-09-18T08:33:48Z-
dc.date.available2019-09-18T08:33:48Z-
dc.date.issued2016-
dc.identifier.citationAngewandte Chemie - International Edition, 2016, v. 55, n. 17, p. 5299-5303-
dc.identifier.issn1433-7851-
dc.identifier.urihttp://hdl.handle.net/10722/276503-
dc.description.abstract© 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim. Described is a new hydrazone-based exo-directing group (DG) strategy developed for the functionalization of unactivated primary β C-H bonds of aliphatic amines. Conveniently synthesized from protected primary amines, the hydrazone DGs are shown to site-selectively promote the β-acetoxylation and tosyloxylation via five-membered exo-palladacycles. Amines with a wide scope of skeletons and functional groups are tolerated. Moreover, the hydrazone DG can be readily removed, and a one-pot C-H acetoxylation/DG removal protocol was also discovered. All about the DGs: A hydrazone-based exo-directing group (DG) strategy is developed for the functionalization of unactivated primary β C-H bonds of aliphatic amines. The hydrazone DGs can be conveniently installed and removed, and promote β-acetoxylation and tosyloxylation via a five-membered exo-palladacycle. PG=protecting group, Ts=4-toluenesulfonyl.-
dc.languageeng-
dc.relation.ispartofAngewandte Chemie - International Edition-
dc.subjectPalladium-
dc.subjectAmines-
dc.subjectC-H activation-
dc.subjectHydrazones-
dc.subjectOxidation-
dc.titleA Hydrazone-Based exo-Directing-Group Strategy for β C-H Oxidation of Aliphatic Amines-
dc.typeArticle-
dc.description.natureLink_to_subscribed_fulltext-
dc.identifier.doi10.1002/anie.201600912-
dc.identifier.scopuseid_2-s2.0-84961775794-
dc.identifier.volume55-
dc.identifier.issue17-
dc.identifier.spage5299-
dc.identifier.epage5303-
dc.identifier.eissn1521-3773-
dc.identifier.isiWOS:000374564300033-

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