100306-31-8Relevant academic research and scientific papers
The Synthesis of Oxiranes and Oxetanes from 1,2- or 1,3-Halohydrins Using Organoantimony(V) Alkoxide
Fujiwara, Masahiro,Hitomi, Kazuhisa,Baba, Akio,Matsuda, Haruo
, p. 106 - 109 (1990)
Tetraphenylstibonium methoxide (1) is an effictive reagent for the synthesis of oxiranes and oxetanes from the corresponding 1,2- and 1,3-halohydrins, respectively.As the reaction conditions are neutral, oxiranes bearing an ester moiety were obtained intact without undergoing solvolysis.In addition, oxetanes, whose preparation was not generally facile, were formed in good yields under mild conditions (60-80 deg C).
Ni-Catalyzed Formal Cross-Electrophile Coupling of Alcohols with Aryl Halides
Lin, Quan,Ma, Guobin,Gong, Hegui
, p. 14102 - 14109 (2021/11/20)
Direct coupling of unactivated alcohols remains a challenge in current synthetic chemistry. We herein demonstrate a strategy building upon in situ halogenation/reductive coupling of alcohols with aryl halides to forge Csp2-Csp3 bonds. The combination of 2-chloro-3-ethylbenzo[d]oxazol-3-ium salt (CEBO) and TBAB as the mild bromination reagents enables rapid transformation of a wide range of alcohols to their bromide counterparts within one to 5 min in CH3CN and DMF, which is compatible with the Ni-catalyzed cross-electrophile coupling conditions in the presence of a chemical reductant. The present method is suitable for arylation of a myriad of structurally complex alcohols with no need for prepreparation of alkyl halides. More importantly, the mild and kinetically rapid bromination process has shown good selectivity in the bromination/arylation of symmetric diols and less sterically hindered hydroxyl groups in polyols, thus offering promise for selective functionalization of diols and polyols without laborious protecting/deprotecting operations. The practicality of this work is also evident in the arylation of a number of carbohydrates, drug compounds, and naturally occurring alcohols.
Intermolecular Electrophilic Bromoesterification and Bromoetherification of Unactivated Cyclopropanes
Leung, Vincent Ming-Yau,Gieuw, Matthew H.,Ke, Zhihai,Yeung, Ying-Yeung
, p. 2039 - 2044 (2020/04/20)
1,3-difunctionalization of cyclopropane is an useful organic transformation. The corresponding 1,3-difunctionalized products are synthetic synthons and building blocks in many organic syntheses. Many existing ring-opening difunctionalization methodologies rely primarily on the use of donor?acceptor cyclopropanes, while the difunctionalization of unactivated cyclopropanes is less exploited. In this research, 1,3-bromoesterification and 1,3-bromoetherification of unactivated cyclopropanes were successfully achieved using N-bromosuccinimide as the brominating agent with high yields and regioselectivity. (Figure presented.).
Copper-Catalyzed C-H Fluorination/Functionalization Sequence Enabling Benzylic C-H Cross Coupling with Diverse Nucleophiles
Buss, Joshua A.,Golden, Dung L.,Stahl, Shannon S.,Vasilopoulos, Aristidis
supporting information, (2020/08/24)
Site-selective transformation of benzylic C-H bonds into diverse functional groups is achieved via Cu-catalyzed C-H fluorination with N-fluorobenzenesulfonimide (NFSI), followed by substitution of the resulting fluoride with various nucleophiles. The benzyl fluorides generated in these reactions are reactive electrophiles in the presence of hydrogen-bond donors or Lewis acids, allowing them to be used without isolation in C-O, C-N, and C-C coupling reactions.
