title: Bismuth compounds in organic synthesis. A one-pot synthesis of homoallyl ethers and homoallyl acetates from aldehydes catalyzed by bismuth triflate.
abstract: [reaction: see text] Three one-pot methods for the conversion of aldehydes to homoallyl ethers catalyzed by Bi(OTf)(3).xH(2)O (1 < x < 4) have been developed. The one-pot synthesis of homoallyl ethers can be achieved either by in situ generation of the acetal followed by its reaction with allyltrialkylsilane or by a three-component synthesis in which the aldehyde, trimethylorthoformate or an alkoxytrimethylsilane and allyltrimethylsilane are mixed together in the presence of bismuth triflate (0.1-1.0 mol %). In addition, a three-component synthesis of homoallyl acetates, which is achieved by reacting the aldehyde, acetic anhydride, and allyltrimethylsilane in the presence of bismuth triflate (3.0-5.0 mol %), has been developed. The use of a relatively nontoxic, easy to handle, and inexpensive catalyst adds to the versatility of these methods.
authors.affiliation: Laboratory for Environment Friendly Organic Synthesis, Department of Chemistry, Illinois Wesleyan University, Bloomington, Illinois 61701.
authors.forename: Peter W
authors.initials: PW
authors.lastname: Anzalone
authors.forename: Ashvin R
authors.initials: AR
authors.lastname: Baru
authors.forename: Eric M
authors.initials: EM
authors.lastname: Danielson
authors.forename: Patrick D
authors.initials: PD
authors.lastname: Hayes
authors.forename: Mai P
authors.initials: MP
authors.lastname: Nguyen
authors.forename: Ambrose F
authors.initials: AF
authors.lastname: Panico
authors.forename: Russell C
authors.initials: RC
authors.lastname: Smith
authors.forename: Ram S
authors.initials: RS
authors.lastname: Mohan
mesh_terms: D000085:Acetates / Q000138:chemical synthesis*; D000447:Aldehydes / Q000138:chemical synthesis / Q000737:chemistry*; D000498:Allyl Compounds / Q000138:chemical synthesis / Q000737:chemistry*; D002384:Catalysis; D004952:Esters / Q000138:chemical synthesis*; D008698:Mesylates / Q000737:chemistry*; D008968:Molecular Conformation; D009942:Organometallic Compounds / Q000737:chemistry*
chemical_list: D000085:Acetates; D000447:Aldehydes; D000498:Allyl Compounds; D004952:Esters; D008698:Mesylates; D009942:Organometallic Compounds; C445789:Bi(OTf)3