Catalytic Use of Indium(0) for Carbon−Carbon Bond Transformations in Water: General Catalytic Allylations of Ketones with Allylboronates

Uwe Schneider, Masaharu Ueno, Shu Kobayashi

Research output: Contribution to journalArticlepeer-review

Abstract

We have discovered the unprecedented catalytic use of In(0) for catalytic C-C bond transformations. Remarkably, these general catalytic allylations of ketones proceeded smoothly in water as a sole solvent under mild conditions, and water proved to be essential for these reactions. Both the displayed substrate scope and the functional group tolerance were excellent. Importantly, the In metal catalyst could be easily recovered and reused without loss of catalytic activity. Moreover, when an alpha-adduct. Additionally, the resulting tertiary homoallylic alcohols were obtained with exceptionally high diastereoselectivities. The applicability of this concept to asymmetric catalysis in water by using In(0) combined with a chiral bis(oxazoline) ligand was demonstrated as well.

Original languageEnglish
Pages (from-to)13824-13825
Number of pages2
JournalJournal of the American Chemical Society
Volume130
Issue number42
DOIs
Publication statusPublished - 22 Oct 2008

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