Evaluation of Cyclic Amides as Activating Groups in N–C Bond Cross-Coupling: Discovery of N -Acyl-δ-valerolactams as Effective Twisted Amide Precursors for Cross-Coupling Reactions
- Award ID(s):
- 1650766
- PAR ID:
- 10323760
- Date Published:
- Journal Name:
- The Journal of Organic Chemistry
- Volume:
- 86
- Issue:
- 15
- ISSN:
- 0022-3263
- Page Range / eLocation ID:
- 10455 to 10466
- Format(s):
- Medium: X
- Sponsoring Org:
- National Science Foundation
More Like this
-
Nitrogen-containing heterocycles represent the majority of FDA-approved small-molecule pharmaceuticals. Herein, we describe a synthetic method to produce saturated N-heterocyclic drug scaffolds with an internal alkyne for elaboration. The treatment of N,N-dimethylhydrazinoalkenes with Et2Zn, followed by a Cu(I)-catalyzed cross-coupling with 1-bromoalkynes, results in piperidines and pyrrolidines with a good yield. Five examples are reported and a proposed mechanism for the Cu(I)-catalyzed cross-coupling is presented.more » « less
An official website of the United States government

