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Ligand-enabled cross-coupling of C(sp3)-H bonds with arylboron reagents via Pd(II)/Pd(0) catalysis.
- Source :
-
Nature Chemistry . Feb2014, Vol. 6 Issue 2, p146-150. 5p. - Publication Year :
- 2014
-
Abstract
- There have been numerous developments in C-H activation reactions in the past decade. Attracted by the ability to functionalize molecules directly at ostensibly unreactive C-H bonds, chemists have discovered reaction conditions that enable reactions of C(sp2)-H and C(sp3)-H bonds with a variety of coupling partners. Despite these advances, the development of suitable ligands that enable catalytic C(sp3)-H bond functionalization remains a significant challenge. Herein we report the discovery of a mono-N-protected amino acid ligand that enables Pd(II)-catalysed coupling of γ-C(sp3)-H bonds in triflyl-protected amines with arylboron reagents. Remarkably, no background reaction was observed in the absence of ligand. A variety of amine substrates and arylboron reagents were cross-coupled using this method. Arylation of optically active substrates derived from amino acids also provides a potential route for preparing non-proteinogenic amino acids. [ABSTRACT FROM AUTHOR]
Details
- Language :
- English
- ISSN :
- 17554330
- Volume :
- 6
- Issue :
- 2
- Database :
- Academic Search Index
- Journal :
- Nature Chemistry
- Publication Type :
- Academic Journal
- Accession number :
- 93883879
- Full Text :
- https://doi.org/10.1038/nchem.1836