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Synfacts 2021; 17(05): 0543
DOI: 10.1055/s-0040-1720471
Polymer-Supported Synthesis

Benzylic C–H Borylation on Ceria-Supported Nickel Hydroxides

Contributor(s):
Yasuhiro Uozumi
,
Aya Tazawa
Yoshii D, Yatabe T, Yabe T, Yamaguchi K. * The University of Tokyo, Japan
C(sp3)–H Selective Benzylic Borylation by In Situ Reduced Ultrasmall Ni Species on CeO2 .

ACS Catal. 2021;
11: 2150-2155
DOI: 10.1021/acscatal.1c00185.
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Key words

C–H activation - borylation - nickel catalysis

Significance

Nickel hydroxides supported on CeO2 (Ni(OH) x /CeO2), prepared by mixing NiCl·6H2O and CeO2 in H2O (pH = 10) (eq. 1), catalyzed the benzylic C–H borylation of alkylarenes or diphenylmethanes with pinacolborane to give the corresponding benzylic boronates (eq. 2). In the reaction of methylarenes, gem-diborylated products were obtained as the main products (eq. 3). The monoborylation of methylarenes was also achieved by using the catalyst pretreated with HBpin and with the methylarene as the solvent (eq. 4).


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Comment

Ni(OH)x/CeO2 was characterized by means of XANES XPS, EXAFS, HAADF-STEM, STEM-EDS, XRD, and ICP-AES analyses. A hot-filtration experiment suggested that the reaction occurred heterogeneously.


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Publication History

Article published online:
20 April 2021

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