Issue 16, 2023

The B[double bond, length as m-dash]C bond: some recent developments

Abstract

The negatively charged borataalkenes and the neutral boraalkenes are isolable organoelement compounds that contain B[double bond, length as m-dash]C double bonds. The use of strongly electron withdrawing fluoroaryl substituents at boron greatly facilitates the preparation of these systems. The (C6F5)2B containing boranes show greatly enhanced α-CH acidicties. This favours the formation of the corresponding borataalkenes by deprotonation. Several synthetic routes to reactive boraalkenes have been developed that make use of fluoroaryl containing B–H borenium cations. The borataalkenes serve as active borata-Wittig olefination reagents. Many boraalkenes undergo [2 + 2] cycloaddition reactions at the B[double bond, length as m-dash]C double bond with various unsaturated organic reagents. Both the borataalkenes and boraalkenes may serve as π-ligands in organometallic and coordination chemistry.

Graphical abstract: The B [[double bond, length as m-dash]] C bond: some recent developments

Article information

Article type
Chemistry Frontiers
Submitted
30 may 2023
Accepted
05 iyl 2023
First published
11 iyl 2023

Org. Chem. Front., 2023,10, 4161-4166

The B[double bond, length as m-dash]C bond: some recent developments

C. Chen, G. Kehr and G. Erker, Org. Chem. Front., 2023, 10, 4161 DOI: 10.1039/D3QO00796K

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