Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 141, Issue 24, Pages 9739-9745Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jacs.9b05074
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Funding
- European Research Council (ERC Starting Grant) [306793 - CASAA]
- ETH Zurich
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Spiro- and bridged bicyclic structures are in demand for their sp(3)-rich frameworks that offer unique physiochemical properties and precisely positioned substituent groups. In order to rapidly access such molecules in a crosscoupling fashion we describe olefin amine (OLA) reagents for the transformation of aldehydes and ketones into all three topological types of bicyclic N-heterocycles: bridged, spiro-, and fused rings. The OLA reagents are easily prepared and allow the synthesis of complex molecular frameworks under operationally simple conditions that tolerate a wide array of functional groups. Investigations into the Mn or Fe promoted reaction pathway support a metal hydride hydrogen atom transfer (MH-HAT) to generate a C-centered radical that undergoes addition to an unactivated imine, leading to an N-centered radical. A catalytic cycle featuring regeneration of the metal catalyst by O-2 and a second HAT to form the unprotected saturated N-heterocycle appears to be operative.
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