Lewis base activation of Lewis acids: development of a Lewis base catalyzed selenolactonization.
The concept of Lewis base activation of Lewis acids has been applied to the selenolactonization reaction. Through the use of substoichiometric amounts of Lewis bases with "soft" donor atoms (S, Se, P) significant rate enhancements over the background reaction are seen. Preliminary mechanistic investigations have revealed the resting state of the catalyst as well as the significance of a weak Brønsted acid promoter.
Denmark
Scott E
SE
Roger Adams Laboratory, Department of Chemistry, University of Illinois, 600 South Mathews Avenue, Urbana, Illinois 61801, USA. denmark@scs.uiuc.edu
Collins
William R
WR
D000143:Acids / Q000737:chemistry*; D000468:Alkalies / Q000737:chemistry*; D002264:Carboxylic Acids / Q000737:chemistry; D002384:Catalysis; D004583:Electrons; D006863:Hydrogen-Ion Concentration; D007783:Lactones / Q000138:chemical synthesis / Q000737:chemistry*; D015394:Molecular Structure; D011522:Protons; D018036:Selenium Compounds / Q000138:chemical synthesis* / Q000737:chemistry
D000143:Acids; D000468:Alkalies; D002264:Carboxylic Acids; D007783:Lactones; D011522:Protons; D018036:Selenium Compounds