Issue 14, 2021

Synthesis, structures and catalytic activity of some BINOL based boronates and boronium salts

Abstract

The BINOL supported chiral boronate ester [C10H12O2BC6F5(THF)] [(R)-1], [C10H12O2BC6F5(O[double bond, length as m-dash]PEt3)] [(R)-3] and [C10H12O2BC6F5]2 [(R,R)-2] as well as the chiral boronium salts [C10H12O2B(O[double bond, length as m-dash]PEt3)2]+[B(O2C10H12)2], [(R)-6] and [C10H12O2B(O[double bond, length as m-dash]SMe2)2]+[B(O2C10H12)2] [(R)-7] have been synthesized, characterized by NMR spectroscopy, and the solid state structures of [(R)-1], [(R,R)-2] and [(R)-3] determined. Chiral ester [(R)-1] was found to be a potent Lewis acid, similar to B(C6F5)3, and capable of rapidly catalyzing the annulation of (R)-, (S)- and rac-styrene oxide with nitrone PhCH[double bond, length as m-dash]N(O)Me to trans-2-methyl-3,6-diphenyl-1,4,2-dioxazine (trans-11) with high regio- and diastereoslectivities.

Graphical abstract: Synthesis, structures and catalytic activity of some BINOL based boronates and boronium salts

Supplementary files

Article information

Article type
Paper
Submitted
13 Mar 2021
Accepted
23 Mar 2021
First published
23 Mar 2021

Dalton Trans., 2021,50, 5044-5049

Synthesis, structures and catalytic activity of some BINOL based boronates and boronium salts

S. Garg, D. K. Unruh and C. Krempner, Dalton Trans., 2021, 50, 5044 DOI: 10.1039/D1DT00842K

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