15232-10-7Relevant articles and documents
Progress towards metal-free radical alkylations of quinones under mild conditions
Galloway, Jordan D.,Baxter, Ryan D.
, (2019)
A new method for the radical alkylation of quinones is reported. Lewis basic nitrogen additives increase the efficacy of quinone alkylations from carboxylic acids using catalytic AgNO3 and Selectfluor as a mild oxidant. Electrochemical data sug
Quinone C-H Alkylations via Oxidative Radical Processes
Hamsath, Akil,Galloway, Jordan D.,Baxter, Ryan D.
, p. 2915 - 2923 (2018/06/12)
A brief survey of radical additions to quinones is reported. Carboxylic acids, aldehydes, and unprotected amino acids are compared as alkyl radical precursors for the mono- or bis- C-H alkylation of several quinones. Two methods for radical initiation are discussed comparing inorganic persulfates and Selectfluor as stoichiometric oxidants. Kinetic analysis reveals dramatic differences in the rate of radical initiation depending on the identity of the radical precursor and oxidant. Synthetic strategies for efficiently producing alkyl-quinones are discussed in the context of selecting optimum radical precursors and initiators depending on quinone identity and functional groups present.
Catalytic asymmetric [2+2] cycloaddition between quinones and fulvenes and a subsequent stereoselective isomerization to 2,3-dihydrobenzofurans
Zheng, Haifeng,Xu, Chaoran,Wang, Yan,Kang, Tengfei,Liu, Xiaohua,Lin, Lili,Feng, Xiaoming
supporting information, p. 6585 - 6588 (2017/07/10)
The catalytic enantioselective [2+2] cycloaddition between quinones and fulvenes was achieved, for the first time, by the use of a chiral copper(ii) complex catalyst. The transformation afforded a series of enantiomerically enriched [6,4,5]-tricyclic cyclobutane derivatives in good yields with excellent regio- and stereoselectivities. Furthermore, the [2+2] adducts could be easily converted into formal [3+2] adducts efficiently and stereoselectively.