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Article: A Hydrazone-Based exo-Directing-Group Strategy for β C-H Oxidation of Aliphatic Amines
Title | A Hydrazone-Based exo-Directing-Group Strategy for β C-H Oxidation of Aliphatic Amines |
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Authors | |
Keywords | Palladium Amines C-H activation Hydrazones Oxidation |
Issue Date | 2016 |
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 Identifier | http://hdl.handle.net/10722/276503 |
ISSN | 2023 Impact Factor: 16.1 2023 SCImago Journal Rankings: 5.300 |
ISI Accession Number ID |
DC Field | Value | Language |
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dc.contributor.author | Huang, Zhongxing | - |
dc.contributor.author | Wang, Chengpeng | - |
dc.contributor.author | Dong, Guangbin | - |
dc.date.accessioned | 2019-09-18T08:33:48Z | - |
dc.date.available | 2019-09-18T08:33:48Z | - |
dc.date.issued | 2016 | - |
dc.identifier.citation | Angewandte Chemie - International Edition, 2016, v. 55, n. 17, p. 5299-5303 | - |
dc.identifier.issn | 1433-7851 | - |
dc.identifier.uri | http://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.language | eng | - |
dc.relation.ispartof | Angewandte Chemie - International Edition | - |
dc.subject | Palladium | - |
dc.subject | Amines | - |
dc.subject | C-H activation | - |
dc.subject | Hydrazones | - |
dc.subject | Oxidation | - |
dc.title | A Hydrazone-Based exo-Directing-Group Strategy for β C-H Oxidation of Aliphatic Amines | - |
dc.type | Article | - |
dc.description.nature | link_to_subscribed_fulltext | - |
dc.identifier.doi | 10.1002/anie.201600912 | - |
dc.identifier.scopus | eid_2-s2.0-84961775794 | - |
dc.identifier.volume | 55 | - |
dc.identifier.issue | 17 | - |
dc.identifier.spage | 5299 | - |
dc.identifier.epage | 5303 | - |
dc.identifier.eissn | 1521-3773 | - |
dc.identifier.isi | WOS:000374564300033 | - |
dc.identifier.issnl | 1433-7851 | - |