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Efficient and recyclable Cu2(BPDC)2(DABCO)-catalyzed direct amination of activated sp3 CH bonds by N–H heterocycles

Paper ID Volume ID Publish Year Pages File Format Full-Text
39012 45801 2016 7 PDF Available
Title
Efficient and recyclable Cu2(BPDC)2(DABCO)-catalyzed direct amination of activated sp3 CH bonds by N–H heterocycles
Abstract

•First heterogeneous catalysts for direct couplings of activated sp3 CH with N–H heterocycles.•Catalytic activity of Cu2(BPDC)2(DABCO) is comparable to that of homogeneous Cu salts.•The catalyst can be facilely recovered and reused.

A metal-organic framework Cu2(BPDC)2(DABCO) was successfully synthesized and employed as an efficient heterogeneous catalyst for the direct CN cross-coupling reaction via sp3 CN bond activation between N–H heterocycles and amides. Kinetic investigation was thoroughly conducted. The optimal conditions involve the use of Cu2(BPDC)2(DABCO) catalyst (3%), di-tert-butyl peroxide oxidant (2 equivalents) in chlorobenzene solvent at 120 °C in 2 h. The Cu2(BPDC)2(DABCO) offered higher catalytic activity than that of other Cu-MOFs such as Cu2(BPDC)2(BPY), Cu3(BTC)2 and Cu2(BDC)2(DABCO), and that of several common copper salts such as CuCl, CuBr, CuI, Cu(NO3)2, and CuSO4. To investigate the mechanism, catalyst poisoning experiments and reactions with added radical scavengers were conducted. Furthermore, the catalyst could be recovered and reused several times without much decline in the reaction yield.

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Keywords
Metal-organic framework; Cross-coupling; Azoles; Amides; CN bond activation; Heterogeneous catalyst
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Efficient and recyclable Cu2(BPDC)2(DABCO)-catalyzed direct amination of activated sp3 CH bonds by N–H heterocycles
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Publisher
Database: Elsevier - ScienceDirect
Journal: Applied Catalysis A: General - Volume 510, 25 January 2016, Pages 27–33
Authors
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Subjects
Physical Sciences and Engineering Chemical Engineering Catalysis
Get Full-Text Now
Don't Miss Today's Special Offer
Price was $35.95
You save - $31
Price after discount Only $4.95
100% Money Back Guarantee
Full-text PDF Download
Online Support
Any Questions? feel free to contact us