Tunable Arylative Cyclization of 1,6-Enynes Triggered by Rhodium(III)-Catalyzed C–H Activation,Journal of the American Chemical Society

当前位置： X-MOL 学术 › J. Am. Chem. Soc. › 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.)

Tunable Arylative Cyclization of 1,6-Enynes Triggered by Rhodium(III)-Catalyzed C–H Activation
Journal of the American Chemical Society ( IF 14.4 ) Pub Date : 2014-10-22 , DOI: 10.1021/ja5072702
Yuki Fukui ₁ , Ping Liu ₁ , Qiang Liu ₁ , Zhi-Tao He ₁ , Nuo-Yi Wu ₁ , Ping Tian ₁ , Guo-Qiang Lin ₁

Affiliation

Two tunable arylative cyclizations of cyclohexadienone-containing 1,6-enynes are reported via rhodium(III)-catalyzed C-H activation of O-substituted N-hydroxybenzamides. The use of different O substituents, i.e. O-Piv and O-Me, on the directing group allows the formation of either tetracyclic isoquinolones through an Ⓝ-Michael addition process or hydrobenzofurans through a Ⓒ-Michael addition process. Mechanistic investigations of these two cascade reactions clearly indicated that the C-H bond cleavage process was involved in the turnover-limiting step. Furthermore, the cyclization products could be subjected to various transformations for elaborating the pharmaceutically and synthetically valuable potential. This is the first example of a rhodium(III)-catalyzed arylative cyclization reaction of 1,6-enynes, and the results extend the application realm of Cp*Rh(III)-catalyzed C-H activation cascade reactions.

中文翻译：

由铑 (III) 催化的 C-H 活化触发的 1,6-烯炔的可调芳基环化

通过铑（III）催化的CH活化O-取代的N-羟基苯甲酰胺，报道了含环己二烯酮的1,6-烯炔的两种可调芳基化环化。在导向基团上使用不同的 O 取代基，即 O-Piv 和 O-Me，允许通过Ⓝ-迈克尔加成过程形成四环异喹诺酮或通过Ⓒ-迈克尔加成过程形成氢苯并呋喃。这两个级联反应的机理研究清楚地表明 CH 键裂解过程参与了周转限制步骤。此外，环化产物可以进行各种转化，以发挥药学和合成价值的潜力。这是铑 (III) 催化的 1,6-烯炔芳基化环化反应的第一个例子，

更新日期：2014-10-22

点击分享查看原文

点击收藏

阅读更多本刊新发论文本刊介绍/投稿指南