Continuous-Flow Enantioselective Hydrogenative Enyne Cyclization with Chiral Heterogeneous Rh Catalysts,ACS Catalysis

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Continuous-Flow Enantioselective Hydrogenative Enyne Cyclization with Chiral Heterogeneous Rh Catalysts
ACS Catalysis ( IF 11.3 ) Pub Date : 2024-01-26 , DOI: 10.1021/acscatal.3c05868
Yuki Saito ₁ , Yuki Sato ₁ , Shu̅ Kobayashi ₁

Affiliation

Continuous-flow hydrogenations provide greatly improved reaction efficiency due to the efficient mass-transfer between heterogeneous catalysts and hydrogen gas. However, reported flow hydrogenations were limited to only simple functional group transformations, and the development of sophisticated catalysis such as enantioselective reductive C–C bond formations remains challenging. Herein, we have developed continuous-flow enantioselective cyclization of 1,6-enynes using chiral heterogeneous catalysts supported on heteropoly acid/amine-functionalized SiO₂ composites developed in our group. Investigations under continuous-flow conditions revealed that the tuning of the structure of heteropoly acids and amines could improve the catalyst performance. A variety of substrates could produce products with high yields and enantioselectivities under optimized reaction conditions without leaching of the Rh catalyst. Mechanistic studies revealed the cause of catalyst deactivation of this transformation.

中文翻译：

手性多相 Rh 催化剂的连续流对映选择性氢化烯炔环化

由于非均相催化剂和氢气之间的有效传质，连续流氢化大大提高了反应效率。然而，报道的流动氢化仅限于简单的官能团转化，复杂催化的发展，如对映选择性还原 C-C 键形成仍然具有挑战性。在此，我们使用我们小组开发的杂多酸/胺官能化SiO ₂复合材料负载的手性多相催化剂，开发了1,6-烯炔的连续流对映选择性环化。连续流动条件下的研究表明，调整杂多酸和胺的结构可以提高催化剂性能。在优化的反应条件下，多种底物可以产生高产率和对映选择性的产物，且不会浸出 Rh 催化剂。机理研究揭示了这种转变催化剂失活的原因。

更新日期：2024-01-26

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