Journal
ACS CATALYSIS
Volume 10, Issue 5, Pages 2929-2941Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acscatal.9b04551
Keywords
cyclic amines; C-C cleavage; palladium; strain release; Norrish-Yang; cross-coupling
Categories
Funding
- 2018 Merck Disruptive Chemistry Fellowship
- NSF under the CCI Center for Selective C H Functionalization [CHE-1700982]
- NIH [NIGMS ROI 086374, S 100D024998]
- Bristol-Myers Squibb
- Japan Society for the Promotion of Science (JSPS)
- LMU PROSA
- DAAD
- CCHF CSURP program
- Amgen scholar program
- NIH Shared Instrument grant [S10-RR027172]
- NSF MRI-R2 grant [CHE-0958205]
- National Science Foundation of China [NSFC 21702126]
- China Scholarship Council
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Saturated cyclic amines (aza-cycles) are ubiquitous structural motifs found in pharmaceuticals, agrochemicals, and bioactive natural products. Given their importance, methods that directly functionalize aza-cycles are in high demand. Herein, we disclose a fundamentally different approach to functionalizing cyclic amines which relies on C-C cleavage and attendant cross-coupling. The initial functionalization step is the generation of underexplored N-fused bicyclo alpha-hydroxy-beta-lactams under mild, visible light conditions using a Norrish-Yang process to affect alpha-functionalization of saturated cyclic amines. This approach is complementary to previous methods for the C-H functionalization of aza-cycles and provides unique access to various cross-coupling adducts. In the course of these studies, we have also uncovered an orthogonal, base-promoted opening of the N-fused bicyclo alpha-hydroxy-beta-lactams. Computational studies have provided insight into the origin of the complementary C-C cleavage processes.
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