A one-pot allylation-hydrostannation sequence with recycling of the intermediate tin waste.
A one-pot allylation and hydrostannation of alkynals where the tin byproduct formed in the first step of the reaction is recycled and used in the second step of the sequence is presented. Specifically, a BF3·OEt2-promoted allylstannation of the aldehyde moiety in the alkynal is followed by the introduction of polymethylhydrosiloxane (PMHS) and catalytic B(C6F5)3, which convert the tin byproduct of the allylation into Bu3SnH, which then hydrostannates the alkyne in the molecule. (119)Sn and (11)B NMR data suggest an organotin fluoride species is formed during the allylation step and involved in the tin recycling step.
Department of Chemistry, Michigan State University , 578 S. Shaw Lane, East Lansing, Michigan 48824, United States.
Banibrata
B
Ghosh
Maria Del Rosario I
Mdel R
Amado-Sierra
Daniel
D
Holmes
Robert E
RE
Maleczka