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Cross-metathesis of Allenes. Mechanistic Analysis and Identification of a Ru-CAAC as the Most Effective Catalyst
Journal of the American Chemical Society ( IF 15.0 ) Pub Date : 2021-11-30 , DOI: 10.1021/jacs.1c11453
Stella A Gonsales 1 , Zoé C Mueller 1 , Fengyue Zhao 2 , Paulo H S Paioti 1 , Lydia Karmazin 1 , Jing Wan 3 , Fang Liu 2 , K N Houk 4 , Amir H Hoveyda 1, 3
Affiliation  

The first examples of cross-metathesis between two different allenes is disclosed. First- and second-generation Ru complexes were found to be ineffective, at most affording only oligomeric products. The exception was a first-generation complex bearing a bidentate phenyl isopropoxy ligand (i.e., PCy3 is not released upon initiation), reactions with which afforded a 1,3-disubstituted allenyl boronate in 22% yield. On the basis of mechanistic studies designed to gain deeper understanding of the reasons for the ineffectiveness of different Ru catalysts, it was discovered that phosphine-free Ru-CAAC complexes have the steric and electronic attributes to be highly effective. The results of these investigations pave the way for development of additional olefin metathesis reactions that generate allenes.

中文翻译:

艾伦的交叉复​​分解。Ru-CAAC作为最有效催化剂的机理分析和鉴定

公开了两种不同丙二烯之间的交叉复分解的第一个例子。发现第一代和第二代 Ru 配合物无效,最多只能提供低聚产品。例外的是带有双齿苯基异丙氧基配体的第一代复合物(即,PCy 3在引发时不释放),与之反应以 22% 的产率得到 1,3-二取代的硼酸烯基酯。在旨在深入了解不同Ru催化剂无效原因的机理研究的基础上,发现无膦Ru-CAAC配合物具有高效的空间和电子属性。这些研究的结果为开发产生丙二烯的其他烯烃复分解反应铺平了道路。
更新日期:2021-12-15
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