Calcium carbonate as heterogeneous support for recyclable organocatalysts

被引:15
作者
Lizandara-Pueyo, Carlos [1 ,2 ]
Fan, Xinyuan [1 ,3 ,4 ]
Ayats, Carles [1 ,5 ]
Pericas, Miquel A. [1 ,6 ]
机构
[1] Barcelona Inst Sci & Technol, Inst Chem Res Catalonia ICIQ, Avda Paisos Catalans 16, E-43007 Tarragona, Spain
[2] BASF SE, Carl Bosch Str 38, D-67056 Ludwigshafen, Germany
[3] Peking Univ, Coll Chem & Mol Engn, Synthet & Funct Biomol Ctr, Dept Chem Biol,Beijing Natl Lab Mol Sci, Beijing 100871, Peoples R China
[4] Chinese Acad Sci, Shanghai Inst Mat Med, State Key Lab Drug Res, Shanghai 201203, Peoples R China
[5] Leitat Technol Ctr, Carrer Innovacio 2, Terrassa 08225, Spain
[6] Univ Barcelona UB, Dept Quim Inorgan & Organ, Barcelona 08028, Spain
基金
中国国家自然科学基金; 国家重点研发计划;
关键词
Solid-supported catalysis; Calcium carbonate; Surface functionalization; Click chemistry; Asymmetric catalysis; Catalyst recycling; Continuous flow processes;
D O I
10.1016/j.jcat.2020.11.013
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 controlled synthesis of calcium carbonate particles surface-functionalized with azido groups and its subsequent copper-catalyzed alkyne-azide cycloaddition (CuAAC) reactions with organocatalysts bearing alkyne anchors allowed the preparation of novel catalytic materials. A calcium carbonate-supported alpha,alpha-diarylprolinol silyl ether prepared in this manner catalyzes Michael addition of aldehydes to trans-beta-nitrostyrenes with very high diastereo-and enantioselectivity. The immobilized catalyst can be recovered by simple decantation and reused. In addition, this heterogeneous catalytic system can also be adapted to continuous-flow operation, affording a five-fold productivity increase in comparison with the batch process. (C) 2020 Elsevier Inc. All rights reserved.
引用
收藏
页码:107 / 115
页数:9
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