15116-19-5Relevant articles and documents
A Catalytic Oxidative Quinone Heterofunctionalization Method: Synthesis of Strongylophorine-26
Yu, Wanwan,Hjerrild, Per,Jacobsen, Kristian M.,Tobiesen, Henriette N.,Clemmensen, Line,Poulsen, Thomas B.
supporting information, p. 9805 - 9809 (2018/07/31)
The preparation of heteroatom-substituted p-quinones is ideally performed by direct addition of a nucleophile followed by in situ reoxidation. Albeit an appealing strategy, the reactivity of the p-quinone moiety is not easily tamed and no broadly applicable method for heteroatom functionalization exists. Shown herein is that Co(OAc)2 and Mn(OAc)3?2 H2O act as powerful catalysts for oxidative p-quinone functionalization with a collection of O, N, and S nucleophiles, using oxygen as the terminal oxidant. Preliminary mechanistic observations and the first synthesis of the cytotoxic natural product strongylophorine-26 is presented.
Regioselective alkylation of substituted quinones by trialkylboranes
Bieber, Lothar W.,Rolim Neto, Pedro J.,Generino, Regina M.
, p. 4473 - 4476 (2007/10/03)
2-Methoxy-1,4-benzoquinone can be alkylated selectively with trialkrylboranes in position 5, giving high yields of 5-alkyl-2-methoxy-1,4- benzoquinones after oxidative work up. In the case of 2-hydroxy- 1,4naphthoquinone, the same procedure leads to 3-alkylated products. A radical chain mechanism is proposed to explain the observed selectivity.
