Iridium‐Catalyzed Reductive Alkylations of Secondary Amides
Reported herein is the first direct, metal‐catalyzed reductive functionalization of secondary amides to give functionalized amines and heterocycles. The method is shown to have exceptionally broad scope with respect to suitable nucleophiles, which cover both hard and soft C nucleophiles as well as a...
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| Published in | Angewandte Chemie International Edition Vol. 57; no. 35; pp. 11354 - 11358 |
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| Main Authors | , , , , |
| Format | Journal Article |
| Language | English |
| Published |
WEINHEIM
Wiley
27.08.2018
Wiley Subscription Services, Inc |
| Edition | International ed. in English |
| Subjects | |
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| Abstract | Reported herein is the first direct, metal‐catalyzed reductive functionalization of secondary amides to give functionalized amines and heterocycles. The method is shown to have exceptionally broad scope with respect to suitable nucleophiles, which cover both hard and soft C nucleophiles as well as a P nucleophile. The reaction exhibits good chemoselectivity and tolerates several sensitive functional groups.
A soft touch: A versatile, direct, metal‐catalyzed reductive functionalization reaction of secondary amides, to give functionalized amines and heterocycles, was developed. A broad substrate scope for both the amide and nucleophile was observed. Viable nucleophiles include reactive and soft C nucleophiles as well as a P nucleophile. The reaction exhibits good chemoselectivity and tolerates several sensitive functional groups (FGs). |
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| AbstractList | Reported herein is the first direct, metal‐catalyzed reductive functionalization of secondary amides to give functionalized amines and heterocycles. The method is shown to have exceptionally broad scope with respect to suitable nucleophiles, which cover both hard and soft C nucleophiles as well as a P nucleophile. The reaction exhibits good chemoselectivity and tolerates several sensitive functional groups.
A soft touch: A versatile, direct, metal‐catalyzed reductive functionalization reaction of secondary amides, to give functionalized amines and heterocycles, was developed. A broad substrate scope for both the amide and nucleophile was observed. Viable nucleophiles include reactive and soft C nucleophiles as well as a P nucleophile. The reaction exhibits good chemoselectivity and tolerates several sensitive functional groups (FGs). Reported herein is the first direct, metal‐catalyzed reductive functionalization of secondary amides to give functionalized amines and heterocycles. The method is shown to have exceptionally broad scope with respect to suitable nucleophiles, which cover both hard and soft C nucleophiles as well as a P nucleophile. The reaction exhibits good chemoselectivity and tolerates several sensitive functional groups. Reported herein is the first direct, metal-catalyzed reductive functionalization of secondary amides to give functionalized amines and heterocycles. The method is shown to have exceptionally broad scope with respect to suitable nucleophiles, which cover both hard and soft C nucleophiles as well as a P nucleophile. The reaction exhibits good chemoselectivity and tolerates several sensitive functional groups.Reported herein is the first direct, metal-catalyzed reductive functionalization of secondary amides to give functionalized amines and heterocycles. The method is shown to have exceptionally broad scope with respect to suitable nucleophiles, which cover both hard and soft C nucleophiles as well as a P nucleophile. The reaction exhibits good chemoselectivity and tolerates several sensitive functional groups. Reported herein is the first direct, metal-catalyzed reductive functionalization of secondary amides to give functionalized amines and heterocycles. The method is shown to have exceptionally broad scope with respect to suitable nucleophiles, which cover both hard and soft Cnucleophiles as well as a Pnucleophile. The reaction exhibits good chemoselectivity and tolerates several sensitive functional groups. |
| Author | Chen, Hang Han, Feng Hu, Xiu‐Ning Ou, Wei Huang, Pei‐Qiang |
| Author_xml | – sequence: 1 givenname: Wei surname: Ou fullname: Ou, Wei organization: Xiamen University – sequence: 2 givenname: Feng surname: Han fullname: Han, Feng organization: Xiamen University – sequence: 3 givenname: Xiu‐Ning surname: Hu fullname: Hu, Xiu‐Ning organization: Xiamen University – sequence: 4 givenname: Hang surname: Chen fullname: Chen, Hang organization: Xiamen University – sequence: 5 givenname: Pei‐Qiang orcidid: 0000-0003-3230-0457 surname: Huang fullname: Huang, Pei‐Qiang email: pqhuang@xmu.edu.cn organization: Lanzhou University |
| BackLink | https://www.ncbi.nlm.nih.gov/pubmed/29979492$$D View this record in MEDLINE/PubMed |
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| Issue | 35 |
| Keywords | amides ASYMMETRIC-SYNTHESIS INTERMOLECULAR ADDITION-REACTIONS NUCLEOPHILIC-ADDITION IMINIUM ION TERTIARY METHOXYAMIDES iridium ORGANOZINC REAGENTS N-ACYLIMINIUM IONS homogeneous catalysis DIRECT TRANSFORMATION AMINES reductive alkylation synthetic methods |
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| Notes | Dedicated to Professor Guo‐Qiang Lin on occasion of his 75th birthday These authors contributed equally to this work. ObjectType-Article-1 SourceType-Scholarly Journals-1 ObjectType-Feature-2 content type line 14 content type line 23 |
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| Snippet | Reported herein is the first direct, metal‐catalyzed reductive functionalization of secondary amides to give functionalized amines and heterocycles. The method... Reported herein is the first direct, metal-catalyzed reductive functionalization of secondary amides to give functionalized amines and heterocycles. The method... |
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| SubjectTerms | Alkylation Amides Amines Chemistry Chemistry, Multidisciplinary Functional groups homogeneous catalysis Iridium Nucleophiles Physical Sciences reductive alkylation Science & Technology synthetic methods |
| Title | Iridium‐Catalyzed Reductive Alkylations of Secondary Amides |
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