Palladium-Catalyzed N-Alkylation of Amides and Amines with Alcohols Employing the Aerobic Relay Race Methodology

Possibly because homogeneous palladium catalysts are not typical borrowing hydrogen catalysts and ligands are thus ineffective in catalyst activation under conventional anaerobic conditions, they had not been used in the N-alkylation reactions of amines/amides with alcohols in the past. By employing...

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Bibliographic Details
Published in	Chinese journal of chemistry Vol. 30; no. 10; pp. 2322 - 2332
Main Author	余小春姜澜李强谢嫒媛徐清
Format	Journal Article
Language	English
Published	Weinheim WILEY-VCH Verlag 01.10.2012 WILEY‐VCH Verlag Wiley Wiley Subscription Services, Inc
Subjects	aerobic reaction Alcohols Amides Amines Anaerobic conditions Catalysts Chemistry Chemistry, Multidisciplinary N-alkylation reaction N-烷基化反应 Palladium palladium catalysis Physical Sciences relay race methodology Science & Technology 催化剂活化厌氧条件接力方法论酰胺醇胺钯催化剂 palladium catalysis amides C-BOND FORMATION BORROWING HYDROGEN amines N-alkylation reaction relay race methodology alcohols AROMATIC-AMINES HETEROAROMATIC AMINES BENZYL ALCOHOLS SECONDARY ALCOHOLS COUPLING REACTIONS aerobic reaction SELECTIVE SYNTHESIS METAL REDUCTIVE AMINATION
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ISSN	1001-604X 1614-7065 1614-7065
DOI	10.1002/cjoc.201200462

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Summary:	Possibly because homogeneous palladium catalysts are not typical borrowing hydrogen catalysts and ligands are thus ineffective in catalyst activation under conventional anaerobic conditions, they had not been used in the N-alkylation reactions of amines/amides with alcohols in the past. By employing the aerobic relay race methodol- ogy with Pd-catalyzed aerobic alcohol oxidation being a more effective protocol for alcohol activation, ligand-free homogeneous palladiums are successfully used as active catalysts in the dehydrative N-alkylation reactions, giving high yields and selectivities of the alkylated amides and amines. Mechanistic studies implied that the reaction most probably proceeds via the novel relay race mechanism we recently discovered and proposed.
Bibliography:	31-1547/O6 Possibly because homogeneous palladium catalysts are not typical borrowing hydrogen catalysts and ligands are thus ineffective in catalyst activation under conventional anaerobic conditions, they had not been used in the N-alkylation reactions of amines/amides with alcohols in the past. By employing the aerobic relay race methodol- ogy with Pd-catalyzed aerobic alcohol oxidation being a more effective protocol for alcohol activation, ligand-free homogeneous palladiums are successfully used as active catalysts in the dehydrative N-alkylation reactions, giving high yields and selectivities of the alkylated amides and amines. Mechanistic studies implied that the reaction most probably proceeds via the novel relay race mechanism we recently discovered and proposed. palladium catalysis, amides, amines, alcohols, N-alkylation reaction, aerobic reaction, relay racemethodology Yu, Xiaochuna Jiang, Lana Li, Qiang Xie, Yuanyuan Xu, Qing a College of Chemistry and Materials＇ Engineering, Wenzhou University, Wenzhou, Zhejiang 325035, China b . ~ College qf Pharmaceutwal Sctences, Zhejiang University of Technology, Hangzhou, Zhejiang 310014, China ark:/67375/WNG-D2WD88WD-L ArticleID:CJOC201200462 istex:5D73BE73426EB84C2A213B9BB4FDBB9D4A40B83E the Opening Foundation of Zhejing Provincial Top Key Disciplines - No. 100061200123 and 100061200134 SRF for ROCS of SEM, NSF - No. Y4100579 QJTP of Zhejiang Province - No. QJD0902004 NNSFC - No. 20902070 ObjectType-Article-1 SourceType-Scholarly Journals-1 content type line 14
ISSN:	1001-604X 1614-7065 1614-7065
DOI:	10.1002/cjoc.201200462