期刊
JOURNAL OF CATALYSIS
卷 361, 期 -, 页码 407-413出版社
ACADEMIC PRESS INC ELSEVIER SCIENCE
DOI: 10.1016/j.jcat.2018.02.024
关键词
Click chemistry; CuAAC reaction; Intermediate; X-rays; Mechanism
资金
- National Institute of Health [5R01EY013175]
- National Science Foundation [DM-1508722R]
- University of Houston
- Center of Advanced Computing and Data Systems at the University of Houston
- Direct For Mathematical & Physical Scien
- Division Of Materials Research [1508722] Funding Source: National Science Foundation
The CuAAC click reaction is greatly accelerated by tris(triazolylmethyl)amine ligands (TL). Using mass spectrometry, we found a trinuclear TL-Cu-3(I)-acetylide complex formed in the reaction. Under catalytic conditions, the trinuclear complex is more active than the proposed dinuclear complex, whereas in a single-turnover reaction, the dinuclear complex is more reactive. Here, this finding is rationalized by analysis of the first single-crystal X-ray structure of a trinuclear TL-Cu-3(I)-acetylide complex and DFT calculation, revealing how TL stabilizes the trinuclear complex, which may accelerate the reaction by promoting coordination with an azide followed by dissociation of a Cu-I to form a more favorable dinuclear transition state. (C) 2018 Elsevier Inc. All rights reserved.
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