4392-24-9Relevant articles and documents
The Reactivity of Benzyl Lithium Species is Regulated by Intermediate Structures
Kroesen, Ulrike,Knauer, Lena,Strohmann, Carsten
, p. 6232 - 6235 (2017)
The reaction of benzyl lithiums is an important aspect in organic and organometallic synthesis. Reported herein are detailed insights into the reactivity of benzyl lithiums as regulated by intermediate structures. By discussing the carbometalation of allylamines and the reaction of the formed benzyl-lithium compounds with electrophiles, the influence of the metal as well as the solvent on the electronic structure of the intermediate is described. This molecular structure strongly influences the reactivity of these intermediates. By choosing the appropriate reaction conditions, the regioselectivity of reactions with electrophiles can be regulated. With trimethylchlorosilane in n-pentane a selective reaction at the para-position takes place. In contrast, selective reaction at the benzylic position, with trimethylchlorostannane in tetrahydrofuran (THF) as a solvent, is accomplished.
Gold-Catalyzed Formal Hexadehydro-Diels-Alder/Carboalkoxylation Reaction Cascades
Wang, Hong-Fa,Guo, Lin-Na,Fan, Zhi-Bo,Tang, Tian-Hua,Zi, Weiwei
supporting information, p. 2676 - 2681 (2021/04/12)
A dual gold-catalyzed hexadehydro-Diels-Alder/carboalkoxylation cascade reaction is reported. In this transformation, the gold catalyst participated in the hexadehydro-Diels-Alder step, switching the mechanism from a radical type to a cationic one, and then the catalyst activated the resulting aryne to form an ortho-Au phenyl cation species, which underwent a carboalkoxylation rearrangement rather than the expected aryne-ene reaction.
Iridium-catalyzed regio- And enantioselective allylic esterification of secondary allylic alcohols with carboxylic acids
Shao, Ying,Sun, Jiangtao,Tang, Shengbiao,Wang, Changkai,Zhang, Peng
supporting information, p. 11080 - 11083 (2021/10/30)
We report herein an iridium-catalyzed asymmetric allylic esterification of racemic secondary allylic alcohols using free carboxylic acids as nucleophiles under mild conditions with broad functional group tolerance, exhibiting excellent regio- and enantios