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CuBr 2 /TBHP‐Promoted Selective Dibromination and Bromohydroxylation of (Diphenylphosphoryl)allenes
Author(s) -
Liu Tian,
Sun Jing,
Wang Qiang,
Li Lei,
Zhou MingDong
Publication year - 2017
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201700187
Subject(s) - chemistry , substrate (aquarium) , stereoselectivity , scope (computer science) , cascade , combinatorial chemistry , catalysis , reaction conditions , organic chemistry , oceanography , chromatography , computer science , programming language , geology
A cooperative CuBr 2 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.