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Synfacts 2010(6): 0693-0693
DOI: 10.1055/s-0029-1219776
DOI: 10.1055/s-0029-1219776
Metal-Mediated Synthesis
© Georg Thieme Verlag
Stuttgart ˙ New York
Amide-Directed Olefination of sp³ C-H Bonds
Contributor(s):Paul Knochel, Tobias ThalerM. Wasa, K. M. Engle, J.-Q. Yu*
The Scripps Research Institute, La Jolla, USA
Pd(II)-Catalyzed Olefination of sp³ C-H Bonds
J. Am. Chem. Soc. 2010, 132: 3680-3681
The Scripps Research Institute, La Jolla, USA
Pd(II)-Catalyzed Olefination of sp³ C-H Bonds
J. Am. Chem. Soc. 2010, 132: 3680-3681
Further Information
Publication History
Publication Date:
20 May 2010 (online)
Key words
olefination - C-H activation - C-H functionalization - palladium
Significance
A highly efficient protocol for the direct olefination of sp³ C-H bonds was developed. In this reaction, strongly electron-deficient amides serve as directing groups. The method could be applied to a wide variety of substrates, including even cyclopropyl methylene C-H bonds and compounds containing α-hydrogen atoms.
Comment
The scope of the Mizoroki-Heck reaction has been considerably enlarged with this method. Now, not only sp² C-H bonds but also sp³ C-H bonds can be efficiently and selectively olefinated giving an easy and straightforward access to variously functionalized lactams.