Use of a Readily Removable Auxiliary Group for the Synthesis of Pyrrolidones by the Palladium-Catalyzed Intramolecular Amination of Unactivated γ C(sp3)H Bonds

Easy on, easy off: Directing groups found to promote the palladium‐catalyzed amination of γ C(sp3)H and C(sp2)H bonds of secondary amides included 5‐methoxy‐8‐aminoquinoline, which can be removed under mild conditions (see scheme; CAN=ceric ammonium nitrate). In conjunction with a β‐CH methylatio...

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Published inAngewandte Chemie (International ed.) Vol. 52; no. 42; pp. 11124 - 11128
Main Authors He, Gang, Zhang, Shu-Yu, Nack, William A., Li, Qiong, Chen, Gong
Format Journal Article
LanguageEnglish
Published Weinheim WILEY-VCH Verlag 11.10.2013
WILEY‐VCH Verlag
Wiley
Subjects
Amination
auxiliary groups
Chemistry
Chemistry, Multidisciplinary
CH amination
Molecular Structure
palladium
Palladium - chemistry
Physical Sciences
Pyrrolidinones - chemical synthesis
Pyrrolidinones - chemistry
pyrrolidones
Science & Technology
Stereoisomerism
γ-lactams
ACTIVATION
NATURAL-PRODUCTS
ALKYLATION
ARYLATION
pyrrolidones
auxiliary groups
C-H BONDS
FUNCTIONALIZATION
lactams
COOPERATIVE CATALYSIS
CH amination
COUPLING REACTIONS
AROMATIC AMIDES
CONSTRUCTION
palladium
CH amination
γ-lactams
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Summary:Easy on, easy off: Directing groups found to promote the palladium‐catalyzed amination of γ C(sp3)H and C(sp2)H bonds of secondary amides included 5‐methoxy‐8‐aminoquinoline, which can be removed under mild conditions (see scheme; CAN=ceric ammonium nitrate). In conjunction with a β‐CH methylation or γ‐CH arylation step, the γ‐C(sp3)H amination provided access to complex pyrrolidones from readily available precursors.
Bibliography:The Pennsylvania State University
We gratefully acknowledge The Pennsylvania State University, the NSF (CAREER CHE-1055795), and ACS-PRF (51705-DN11) for financial support of this research.
ACS-PRF - No. 51705-DN11
NSF - No. CHE-1055795
ark:/67375/WNG-W7Q1P0VH-J
istex:F89FA8F30A119AA23BA6D3B8E2F38B8F305E8DAC
ArticleID:ANIE201305615
We gratefully acknowledge The Pennsylvania State University, the NSF (CAREER CHE‐1055795), and ACS‐PRF (51705‐DN11) for financial support of this research.
National Science Foundation
ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201305615