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Synfacts 2014; 10(8): 0852
DOI: 10.1055/s-0034-1378488
Metal-Mediated Synthesis
© Georg Thieme Verlag Stuttgart · New York

One-Pot Allylation–Hydrostannation Sequence

Contributor(s):
Paul Knochel
,
Jeffrey M. Hammann
Ghosh B, Amando-Sierra MD. R. I, Holmes D, Maleczka Jr. RE * Michigan State University, East Lansing, USA
A One-Pot Allylation–Hydrostannation Sequence with Recycling of the Intermediate Tin Waste.

Org. Lett. 2014;
16: 2318-2321
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Publication History

Publication Date:
18 July 2014 (online)

 
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Key words

one-pot reaction - allylation - hydrostannation

Significance

The authors report a one-pot allylation and hydrostannation of alkynals in which the in situ formed tin byproduct can be recycled and subsequently used further. A BF3·Et2O-mediated allylstannation of the aldehyde component of the alkynal is followed by the addition of polymethylhydrosiloxane (PMHS) and catalytic B(C6F5)3, which transform the tin byproduct of the allylation into Bu3SnH, which hydrostannates the terminal alkyne.


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Comment

This very unique method selectively affords (Z)-stannanes. Monitoring the reaction via 119Sn and/or 11B NMR showed a Sn_F intermediate amid the BF3·Et2O-mediated reaction between the aldehyde and allyltributylstannane.


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