From Immobilization to Catalyst Use: A Complete Continuous-Flow Approach Towards the Use of Immobilized Organocatalysts

被引：17
作者：
de Oliveira, Pedro H. R. [1 ]
Santos, Bruno M. da S. [1 ]
Leao, Raquel A. C. [2 ]
Miranda, Leandro S. M. [2 ]
San Gil, Rosane A. S. [2 ]
de Souza, Rodrigo O. M. A. [2 ]
Finelli, Fernanda G. [1 ]
机构：
[1] Univ Fed Rio de Janeiro, Inst Pesquisas Prod Nat, BR-21941902 Rio De Janeiro, Brazil
[2] Univ Fed Rio de Janeiro, Inst Quim, BR-21941902 Rio De Janeiro, Brazil
来源：
CHEMCATCHEM | 2019年 / 11卷 / 22期
关键词：
heterogeneous catalysis; enantioselective organocatalysis; continuous-flow; supported organocatalyst; MacMillan's organocatalysts; DIELS-ALDER REACTIONS; ASYMMETRIC ORGANOCATALYSIS; HIGHLY EFFICIENT; SILYL ETHERS; BATCH; ACID;
D O I：
10.1002/cctc.201901129
中图分类号：
O64 [物理化学（理论化学）、化学物理学];
学科分类号：
070304 ; 081704 ;
摘要：
The combination of chiral supported-organocatalysts and flow chemistry promotes the sustainable production of enantioenriched compounds providing a very powerful tool for chemical and pharmaceutical industries. However, the rapid deactivation of these catalysts in heterogeneous asymmetric reactions has been limiting the expansion of the area. In this work we report for the first time the advantages of synthesizing, immobilizing, and using a silica-supported organocatalyst under a complete continuous-flow approach, showing the impact of this method on the morphology, structure and lifetime of the organocatalyst. The first generation MacMillan's organocatalyst was prepared from L-phenylalanine and immobilized in silica through a carbamate linkage under batch and continuous-flow conditions. We also evaluated the performance of both batch and continuous-flow organocatalysts in the Diels-Alder reaction for proof of concept.
引用
收藏
页码：5553 / 5561
页数：9
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