当前位置: X-MOL 学术Angew. Chem. Int. Ed. › 论文详情
Our official English website, www.x-mol.net, welcomes your feedback! (Note: you will need to create a separate account there.)
Copper‐Catalyzed Borocarbonylative Coupling of Internal Alkynes with Unactivated Alkyl Halides: Modular Synthesis of Tetrasubstituted β‐Borylenones
Angewandte Chemie International Edition ( IF 16.6 ) Pub Date : 2018-07-10 , DOI: 10.1002/anie.201804883
Li-Jie Cheng 1 , Neal P. Mankad 1
Affiliation  

Reported is a general procedure to synthesize tetrasubstituted enones, which are borylated in the β‐position, using a copper‐catalyzed four‐component coupling reaction of simple chemical feedstocks: internal alkynes, alkyl halides, bis(pinacolato)diboron (B2pin2), and CO. A broad scope of highly functionalized β‐borylated enones, a largely unknown class of organic compounds, can be accessed efficiently using this method. The synthesis of all‐carbon tetrasubstituted enones was realized by employing the β‐borylated enone unit, without purification, in a Suzuki–Miyaura coupling. The utility of the method was further demonstrated by various transformations, including halogenation, oxidation, and protodeboration, of the corresponding reduced oxaborole species to provide densely substituted allylic alcohol and ketone products.

中文翻译:

内部炔烃与未活化烷基卤化物的铜催化硼羰基偶联:四取代的β-硼烯酮的模块合成

报告了使用简单化学原料通过铜催化的四组分偶联反应合成内部取代的四取代烯酮的一般程序:内炔烃,卤代烷,双(频哪醇)二硼(B 2 pin 2)和一氧化碳。使用这种方法可以有效地获得大量高度官能化的β-硼化烯酮(一种高度未知的有机化合物)。全碳四取代的烯酮的合成是通过在Suzuki-Miyaura偶联中使用未经提纯的β-硼化烯酮单元实现的。通过相应的还原的氧杂硼杂环烷物种的各种转化,包括卤化,氧化和原硼氢化,进一步证明了该方法的实用性,从而提供了稠密取代的烯丙醇和酮产物。
更新日期:2018-07-10
down
wechat
bug