Use of a readily removable auxiliary group for the synthesis of pyrrolidones by the palladium-catalyzed intramolecular amination of unactivated γ C(sp(3))-H bonds

Gang He; Shu-Yu Zhang; William A Nack; Qiong Li; Gong Chen

doi:10.1002/anie.201305615

Use of a readily removable auxiliary group for the synthesis of pyrrolidones by the palladium-catalyzed intramolecular amination of unactivated γ C(sp(3))-H bonds

Angew Chem Int Ed Engl. 2013 Oct 11;52(42):11124-8. doi: 10.1002/anie.201305615. Epub 2013 Aug 27.

Authors

Gang He¹, Shu-Yu Zhang, William A Nack, Qiong Li, Gong Chen

Affiliation

¹ Department of Chemistry, The Pennsylvania State University, 104 Chemistry Building, University Park, PA 16802 (USA).

PMID: 24038874
DOI: 10.1002/anie.201305615

Abstract

Easy on, easy off: Directing groups found to promote the palladium-catalyzed amination of γ C(sp(3) )H and C(sp(2) )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(sp(3) )H amination provided access to complex pyrrolidones from readily available precursors.

Keywords: CH amination; auxiliary groups; palladium; pyrrolidones; γ-lactams.

Publication types

Research Support, Non-U.S. Gov't
Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

Amination
Molecular Structure
Palladium / chemistry*
Pyrrolidinones / chemical synthesis*
Pyrrolidinones / chemistry
Stereoisomerism

Substances

Pyrrolidinones
Palladium