53156-43-7Relevant academic research and scientific papers
Visible-light-promoted radical alkylation/cyclization of allylic amide with N-hydroxyphthalimide ester: Synthesis of oxazolines
Ding, Hao,Huang, Panyi,Jin, Can,Su, Weike,Sun, Bin,Yan, Zhiyang,Zhao, Haiyun
, (2021/10/29)
An efficient photocatalytic alkylation/cyclization of allylic amide with N-hydroxyphthalimide ester has been developed. The transformation is taken advantage of alkyl radicals to attack allylic amide with the assist of inexpensive rose bengal as photocatalyst to prepare a series of alkyl substituted oxazolines in moderate to excellent yields. High regioselectivity, operational safety, mild conditions and excellent substrate generality give this protocol broad application prospects.
Alkene homologation: via visible light promoted hydrophosphination using triphenylphosphonium triflate
Levin, Vitalij V.,Dilman, Alexander D.
, p. 749 - 752 (2021/02/03)
A hydrophosphination reaction of alkenes with triphenylphosphonium triflate under photocatalytic conditions is described. The reaction is promoted by naphthalene-fused N-acylbenzimidazole and is believed to proceed through intermediate formation of a phosphinyl radical cation. The resulting phosphonium salts are directly involved in the Wittig reaction leading to homologated alkenes.
Switch in Selectivity for Formal Hydroalkylation of 1,3-Dienes and Enynes with Simple Hydrazones
Li, Chao-Jun,Lv, Leiyang,Qiu, Zihang,Yu, Lin
supporting information, p. 6466 - 6472 (2020/03/13)
Controlling reaction selectivity is a permanent pursuit for chemists. Regioselective catalysis, which exploits and/or overcomes innate steric and electronic bias to deliver diverse regio-enriched products from the same starting materials, represents a powerful tool for divergent synthesis. Recently, the 1,2-Markovnikov hydroalkylation of 1,3-dienes with simple hydrazones was reported to generate branched allylic compounds when a nickel catalyst was used. As part of the effort, shown here is that a complete switch of Markovnikov to anti-Markovnikov addition is obtained by changing to a ruthenium catalyst, thus providing direct and efficient access to homoallylic products exclusively. Isotopic substitution experiments indicate that no reversible hydro-metallation across the metal-π-allyl system occurred under ruthenium catalysis. Moreover, this protocol is applicable to the regiospecific hydroalkylation of the distal C=C bond of 1,3-enynes.
Visible-light-induced regioselective alkylation of coumarins via decarboxylative coupling with N-hydroxyphthalimide esters
Jin, Can,Yan, Zhiyang,Sun, Bin,Yang, Jin
, p. 2064 - 2068 (2019/04/11)
An efficient photocatalytic decarboxylative 3-position alkylation of coumarins by using alkyl N-hydroxyphthalimide esters as alkylation reagents has been developed. A variety of NHP esters derived from aliphatic carboxylic acids (primary, secondary, and tertiary) has been proved to be tolerated for this decarboxylation process, affording a broad scope of 3-alkylated coumarin derivatives in moderate to excellent yields. This protocol was highlighted by its mild conditions, readily available starting materials, operational simplicity, and wide functional group tolerance.
