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Synfacts 2023; 19(10): 1015
DOI: 10.1055/s-0042-1751593
Polymer-Supported Synthesis

Hydrogenation of N-Heterocycles Using Frustrated Lewis Pairs Incorporated in NU-1000 MOF

Contributor(s):
Yasuhiro Uozumi
,
Aya Tazawa
Xu Z.-M, Hu Z, Huang Y, Bao S.-J, Niu Z, *, Lang J.-P, *, Al-Enizi AM, Nafady A, Ma S. * Soochow University, Suzhou and Shanghai Institute of Organic Chemistry, P. R. of China; University of North Texas, Denton, USA
Introducing Frustrated Lewis Pairs to Metal−Organic Framework for Selective Hydrogenation of N‑Heterocycles.

J. Am. Chem. Soc. 2023;
145: 14994-15000
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Key words

metal organic framework - frustrated Lewis pairs - hydrogenation - N-heterocycles

Significance

Phosphine-borane frustrated Lewis pairs incorporated in MOF (NU-1000-FLP-H2 ) were prepared by treatment 4-(dimesitylphosphanyl)-3-methylbenzoic acid with Zr-based MOF (NU-1000) followed by addition of B(C6F5)3 and reduction with H2 (eq. 1). NU-1000-FLP-H2 catalyzed the hydrogenation of quinolines and indoles with H2 to give the corresponding tetrahydroquinolines and indolines in up to 99% yield (eq. 2).


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Comment

NU-1000-FLP-H2 was characterized by means of 1H NMR, 31P MAS NMR, FT-IR, SEM, TEM, HAADF-STEM, EDS, PXRD, XPS, TGA, N2 isotherms, and elemental analyses. In the hydrogenation of 2-methylquinoline, the catalyst was recovered and reused four times without significant loss of its catalytic activity.


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Publication History

Article published online:
14 September 2023

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