Domino inverse electron-demand Diels-Alder/cyclopropanation reaction of diazines catalyzed by a bidentate Lewis acid.
A domino inverse electron-demand Diels-Alder (IEDDA)/cyclopropanation reaction of diazines was discovered by applying electron-rich furans in the bidentate Lewis acid catalyzed IEDDA reaction. This process produces benzonorcaradienes in excellent yields with a low loading of a bidentate Lewis acid catalyst of 2 to 5 mol %. We demonstrate the broad applicability by 20 examples with different dienophiles and a variety of dienes. A detailed mechanism is proposed supported by DFT calculations.
Department of Chemistry, University of Basel, St. Johanns-Ring 19, Basel 4056, Switzerland.
Simon N
SN
Kessler
Markus
M
Neuburger
Hermann A
HA
Wegner
D000466:Alkadienes / Q000138:chemical synthesis* / Q000737:chemistry*; D002384:Catalysis; D003521:Cyclopropanes / Q000737:chemistry*; D004583:Electrons; D058116:Lewis Acids / Q000737:chemistry*; D015394:Molecular Structure; D011724:Pyridazines / Q000737:chemistry*
D000466:Alkadienes; D003521:Cyclopropanes; D058116:Lewis Acids; D011724:Pyridazines