The preparation of ester heterocycles mostly uses heteroatoms as nucleophilic sites, which are achieved by intramolecular substitution or addition reactions. Compound: 1-(Bromomethyl)-4-iodobenzene( cas:16004-15-2 ) is researched.Related Products of 16004-15-2.Tan, Fei; Pu, Maoping; He, Jun; Li, Jinzhao; Yang, Jian; Dong, Shunxi; Liu, Xiaohua; Wu, Yun-Dong; Feng, Xiaoming published the article 《Catalytic Asymmetric Homologation of Ketones with α-Alkyl α-Diazo Esters》 about this compound( cas:16004-15-2 ) in Journal of the American Chemical Society. Keywords: keto esters chemoselective regioselective enantioselective preparation; alkyl diazoester ketone scandium catalyst homologation chemoselective regioselective enantioselective. Let’s learn more about this compound (cas:16004-15-2).
The homologation of ketones with diazo compounds was a useful strategy to synthesize one-carbon chain-extended acyclic such as PhC(O)CMeCO2MeR [R = allyl, Bn, CH2(2-naphthyl), etc.] or ring-expanded cyclic ketones e.g., I. However, the asym. homologation of acyclic ketones with α-diazo esters remains a challenge due to the lower reactivity and complicated selectivity. Herein, the enantioselective catalytic homologation of acetophenone and related derivatives with α-alkyl α-diazo esters was reported utilizing a chiral scandium(III) N,N’-dioxide as the Lewis acid catalyst. This reaction supplies a highly chemo-, regio-, and enantioselective pathway for the synthesis of optically active β-keto esters with an all-carbon quaternary center through highly selective alkyl-group migration of the ketones. Moreover, the ring expansion of cyclic ketones was accomplished under slightly modified conditions, affording a series of enantioenriched cyclic β-keto esters. D. functional theory calculations was carried out to elucidate the reaction pathway and possible working models that could explain the observed regio- and enantioselectivity.
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Piperazine – Wikipedia,
Piperazines – an overview | ScienceDirect Topics