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ChemInform Abstract: A Novel Cyclization in the Hydroboration of Divinylstannanes.

✍ Scribed by J. A. SODERQUIST; G. LEON

Publisher: John Wiley and Sons
Year: 2010
Weight: 35 KB
Volume: 29
Category: Article
ISSN: 0931-7597
DOI: 10.1002/chin.199829216

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✦ Synopsis

A previously unknown process, the formation of 3-boryl-stannacyclopentane (III), is observed from monohydroboration of divinyldimethyltin (I) with 9-BBN. The product undergoes expected reactions of an organoborane with trimethylamine N-oxide, NaOH/H 2 O 2 , and benzaldehyde. However, attempted Suzuki-Miyaura coupling with bromobenzene results in unexpected formation of 3-butenyl(dimethyl)phenyltin (IX) through an unprecedented "stanna-Heck" process. -(SODERQUIST,

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