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Ligand‐Controlled Palladium(II)‐Catalyzed Regiodivergent Carbonylation of Alkynes: Syntheses of Indolo[3,2‐c]coumarins and Benzofuro[3,2‐c]quinolinones
Angewandte Chemie International Edition ( IF 16.6 ) Pub Date : 2018-06-19 , DOI: 10.1002/anie.201804788
Dong Ding 1 , Guohao Zhu 1 , Xuefeng Jiang 1, 2
Affiliation  

Regiodivergent syntheses of indolo[3,2‐c]coumarins and benzofuro[3,2‐c]quinolinones through a controllable palladium(II)‐catalyzed carbonylative cyclization are established. The chemo‐ and regioselectivity are exclusively tuned by the ligand on the palladium catalyst. The rigid framework of the electron‐deficient ligand promotes the O‐attack/N‐carbonylation cyclization leading to benzofuro[3,2‐c]quinolinones, while a sterically bulky and electron‐rich ligand facilitates N‐attack/O‐carbonylation cyclization to generate indolo[3,2‐c]coumarins. Furthermore, various other nucleophiles are applicable for delivering a variety of indoloquinolinones, pyranoquinolones, and chromeno[3,4‐c]quinolinones in one step, and serves as a method for creating compound libraries for drug discovery.

中文翻译:

配体控制的钯(II)催化炔烃的区域发散性羰基化:吲哚[3,2-c]香豆素和苯并呋喃[3,2-c]喹啉酮的合成

通过可控制的钯(II)催化羰基化环化反应,建立了吲哚[3,2– c ]香豆素和苯并呋喃[3,2– c ]喹啉酮的区域发散性合成。化学和区域选择性仅受钯催化剂上的配体调节。缺电子配体的刚性骨架促进了O-攻击/ N-羰基化环化反应,从而导致苯并呋喃[3,2- c ]喹啉酮,而空间大且富含电子的配体则促进了N-攻击/ O-羰基化环化反应。生成indolo [3,2‐ c]香豆素。此外,其他各种亲核试剂也可用于一步传递各种吲哚喹啉酮,吡喃喹诺酮和色诺[3,4-c]喹啉酮,并且可作为创建用于药物发现的化合物库的方法。
更新日期:2018-06-19
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