Bismuth compounds in organic synthesis. A one-pot synthesis of homoallyl ethers and homoallyl acetates from aldehydes catalyzed by bismuth triflate.
[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.
Anzalone
Peter W
PW
Laboratory for Environment Friendly Organic Synthesis, Department of Chemistry, Illinois Wesleyan University, Bloomington, Illinois 61701.
Baru
Ashvin R
AR
Danielson
Eric M
EM
Hayes
Patrick D
PD
Nguyen
Mai P
MP
Panico
Ambrose F
AF
Smith
Russell C
RC
Mohan
Ram S
RS
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*
D000085:Acetates; D000447:Aldehydes; D000498:Allyl Compounds; D004952:Esters; D008698:Mesylates; D009942:Organometallic Compounds; C445789:Bi(OTf)3