Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 23, Issue 30, Pages 7157-7173Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201605012
Keywords
amide activation; bridged lactams; cross-coupling; N-C activation; twisted amides
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Funding
- Rutgers University
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The concept of using amide bond distortion to modulate amidic resonance has been known for more than 75 years. Two classic twisted amides (bridged lactams) ingeniously designed and synthesized by Kirby and Stoltz to feature fully perpendicular amide bonds, and as a consequence emanate amino-ketone-like reactivity, are now routinely recognized in all organic chemistry textbooks. However, only recently the use of amide bond twist (distortion) has advanced to the general organic chemistry mainstream enabling a host of highly attractive N-C amide bond cross-coupling reactions of broad synthetic relevance. In this Minire-view, we discuss recent progress in this area and present a detailed overview of the prominent role of amide bond destabilization as a driving force in the development of transition-metal-catalyzed cross-coupling reactions by N-C bond activation.
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