化学
亲核细胞
重氮
电泳剂
试剂
催化作用
产量(工程)
卤化
钯
组合化学
偶联反应
有机化学
冶金
材料科学
作者
Ryota Kajihara,Shingo Harada,Jun-ichi Ueda,Tetsuhiro Nemoto
标识
DOI:10.1016/j.tetlet.2018.03.063
摘要
Diazo compounds are frequently used as precursors of metal carbenoids and act as soft nucleophiles even without the use of metal catalysts. The resulting diazonium species may also be trapped by various nucleophiles. The introduction of an iodine functionality applicable for the coupling reaction into an alkenyl diazo compound, however, has not been reported. We developed iodoalkoxylation reactions of alkenyl diazoacetates using an electrophilic iodinating reagent and oxygen nucleophile. This catalyst-free multicomponent reaction proceeded regioselectively, furnishing trisubstituted vinyl iodides in 31%–71% yield. The synthesized iodoalkenes were converted into the corresponding olefins with various functionalities in good yield via Suzuki-Miyaura coupling reactions with arylboronic acids under palladium catalysis to demonstrate the synthetic utility of the developed reaction sequence.
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