A Versatile and Highly Z-Selective Olefin Metathesis Ruthenium Catalyst Based on a Readily Accessible N-Heterocyclic Carbene,ACS Catalysis

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A Versatile and Highly Z-Selective Olefin Metathesis Ruthenium Catalyst Based on a Readily Accessible N-Heterocyclic Carbene
ACS Catalysis ( IF 11.3 ) Pub Date : 2018-03-08 00:00:00 , DOI: 10.1021/acscatal.8b00151
Adrien Dumas _{1,

2} , Robert Tarrieu ₁ , Thomas Vives ₁ , Thierry Roisnel ₃ , Vincent Dorcet ₃ , Olivier Baslé ₁ , Marc Mauduit ₁

Affiliation

A ruthenium catalyst for Z-selective olefin metathesis has been synthesized from a readily accessible N-heterocyclic carbene (NHC) ligand that is prepared using an efficient, practical, and scalable multicomponent synthesis. The desired ruthenium complex with cyclometalated NHC ligand is obtained by means of selective C(sp³)-H activation at the adamantyl fragment and X-ray diffraction analysis unambiguously confirmed the structure of the precatalyst. The catalyst demonstrated attractive catalytic performance in self- and cross-metathesis at low catalyst loading to afford the desired internal olefins with high conversion and very high Z-selectivity (up to >99%). The versatility of the chelated catalyst is illustrated by the high cis-selectivity (up to >98%) and high tacticity control (up to >98% syndiotactic) achieved in ring-opening polymerization, allowing for the production of highly microstructurally controlled norbornene-, norbornadiene-, and cyclopropene-derived polymers.

中文翻译：

基于易于获得的N-杂环碳烯的多功能高Z选择烯烃复分解钌催化剂

Z-选择性烯烃复分解的钌催化剂是由易于获得的N-杂环卡宾（NHC）配体合成的，该配体是使用高效，实用和可扩展的多组分合成方法制备的。借助在金刚烷基片段上的选择性C（sp ³）-H活化获得所需的具有环金属化NHC配体的钌配合物，X射线衍射分析明确证实了前催化剂的结构。该催化剂在低催化剂负载下在自复分解和交叉复分解中表现出有吸引力的催化性能，从而提供具有高转化率和非常高的Z选择性（高达> 99％）的所需内烯烃。螯合催化剂的多功能性由高在开环聚合中实现了顺式选择性（最高> 98％）和高立构规整度（最高> 98％间规），可以生产高度微观结构控制的降冰片烯，降冰片二烯和环丙烯衍生的聚合物。

更新日期：2018-03-08

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