Gold-catalyzed (4+3)-annulations of 2-alkenyl-1-alkynylbenzenes with anthranils with alkyne-dependent chemoselectivity: skeletal rearrangement versus non-rearrangement
化学选择性
炔烃
催化作用
化学
立体化学
有机化学
作者
RahulKumar Rajmani Singh,Manisha Skaria,Liang-Yü Chen,Mu‐Jeng Cheng,Rai‐Shung Liu
出处
期刊:Chemical Science [The Royal Society of Chemistry] 日期:2018-11-12卷期号:10 (4): 1201-1206被引量:61
Two distinct (4+3)-nitroxy annulations between 1,5-enynes and anthranils have been developed to access tetrahydro-1H-benzo[b]azepine derivatives; the chemoselectivity varies with the types of alkynes. Terminal alkyne substrates deliver benzo[b]azepine derivatives via a novel skeletal rearrangement while internal 1,5-enynes afford products without a rearrangement process. To elucidate the mechanism of rearrangement, we performed 13C- and 2H-labeling experiments to identify the gold-containing isobenzofulvene intermediates, but their formation relies on the presence of anthranils.