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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| Published in | Chinese journal of chemistry Vol. 30; no. 10; pp. 2322 - 2332 |
|---|---|
| Main Author | |
| Format | Journal Article |
| Language | English |
| Published |
Weinheim
WILEY-VCH Verlag
01.10.2012
WILEY‐VCH Verlag Wiley Wiley Subscription Services, Inc |
| Subjects | |
| Online Access | Get full text |
| ISSN | 1001-604X 1614-7065 1614-7065 |
| DOI | 10.1002/cjoc.201200462 |
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| Abstract | 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. |
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| AbstractList | 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 methodology 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. 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. 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 methodology 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. By employing the aerobic relay race methodology 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 of amines and amides with alcohols, giving high yields and selectivities of the alkylated amines and amides. Mechanistic studies implied that the reaction most probably proceeds via the novel relay race mechanism we recently discovered and proposed. 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 methodology 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. [PUBLICATION ABSTRACT] 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 methodology 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. |
| Author | Jiang, Lan Yu, Xiaochun Li, Qiang Xu, Qing Xie, Yuanyuan |
| AuthorAffiliation | College of Chemistry and Materials Engineering, Wenzhou University, Wenzhou, Zhejiang 325035, China College qf Pharmaceutical Sciences, Zhejiang University of Technology, Hangzhou, Zhejiang 310014, China |
| Author_xml | – sequence: 1 fullname: 余小春 姜澜 李强 谢嫒媛 徐清 |
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| Copyright | Copyright © 2012 SIOC, CAS, Shanghai & WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim Copyright © 2012 SIOC, CAS, Shanghai & WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim |
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| Keywords | 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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| Notes | 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 |
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| SubjectTerms | 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 |
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| Title | Palladium-Catalyzed N-Alkylation of Amides and Amines with Alcohols Employing the Aerobic Relay Race Methodology |
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