Enantioselective cyanation of benzylic C–H bonds via copper-catalyzed radical relay
Shanghai Institute of Organic Chemistry · University of Chinese Academy of Sciences · +1 more institution
Abstract
Direct methods for stereoselective functionalization of sp 3 -hybridized carbon–hydrogen [C(sp 3 )–H] bonds in complex organic molecules could facilitate much more efficient preparation of therapeutics and agrochemicals. Here, we report a copper-catalyzed radical relay pathway for enantioselective conversion of benzylic C–H bonds into benzylic nitriles. Hydrogen-atom abstraction affords an achiral benzylic radical that undergoes asymmetric C(sp 3 )–CN bond formation upon reaction with a chiral copper catalyst. The reactions proceed efficiently at room temperature with the benzylic substrate as limiting reagent, exhibit broad substrate scope with high enantioselectivity (typically 90 to 99% enantiomeric…
Citation impact
- FWCI
- 51.80
- Percentile
- 100%
- References
- 61
Authors
7- WZWen ZhangCorresponding
Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences
- FWFei WangCorresponding
Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences
- SDScott D. McCann
University of Wisconsin–Madison
- DWDinghai Wang
Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences
- PCPinhong Chen
Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences
Topics & keywords
- Chemistry
- Enantioselective synthesis
- Cyanation
- Radical
- Catalysis
- Combinatorial chemistry
- Substrate (aquarium)
- Hydrogen atom abstraction
Funding
- NSNational Science FoundationAward: CHE-0840494
- UDU.S. Department of EnergyAward: DE-FG02-05ER15690
- NNNational Natural Science Foundation of ChinaAwards: 21225210, 21421091, 21532009, 21472217
- NINational Institutes of HealthAward: F31-GM116443
- NKNational Key Research and Development Program of ChinaAward: 973-2015CB856600