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- Title
CuBr<sub>2</sub>/TBHP-Promoted Selective Dibromination and Bromohydroxylation of (Diphenylphosphoryl)allenes.
- Authors
Liu, Tian; Sun, Jing; Wang, Qiang; Li, Lei; Zhou, Ming‐Dong
- Abstract
A cooperative CuBr2 and tert-butyl hydroperoxide (TBHP) system allowed for the highly stereoselective dibromination and bromohydroxylation reactions of (diphenylphosphoryl)allenes under mild (room temperature) and operationally simple conditions. These reactions selectively proceeded through either a dibromination or bromohydroxylation process and are characterized by their broad substrate scope (22 examples), their step economy, and ability to be carried out on a gram scale. This method offers a useful protocol to access allyl bromides and alcohols. Moreover, synthetic applications of the dibromination products include a Suzuki–Miyaura cross-coupling reaction and copper-catalyzed cascade process, which could also afford various important derivatives.
- Subjects
COPPER alloys; HYDROXYLATION; ALLENE; HYDROPEROXIDES; BROMINATION
- Publication
European Journal of Organic Chemistry, 2017, Vol 2017, Issue 14, p1915
- ISSN
1434-193X
- Publication type
Article
- DOI
10.1002/ejoc.201700187