Synthesis, Characterization, and Functionalization of 1-Boraphenalenes

Angewandte Chemie
Rachel J KahanMichael J Ingleson

Abstract

1-Boraphenalenes have been synthesized by reaction of BBr3 with 1-(aryl-ethynyl)naphthalenes, 1-ethynylnaphthalene, and 1-(pent-1-yn-1-yl)naphthalene and they can be selectively functionalized at boron or carbon to form bench-stable products. All of these 1-boraphenalenes have LUMOs localized on the planar C12 B core that are closely comparable in character to isoelectronic phenalenyl cations. In contrast to the comparable LUMOs, the aromatic stabilization of the C5 B ring in 1-boraphenalenes is dramatically lower than the C6 rings in phenalenyl cations. This is due to the occupied orbitals of π symmetry being less delocalised in the 1-boraphenalenes.

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Citations

Oct 30, 2018·Angewandte Chemie·Di WangZhuangzhi Shi
Jun 5, 2020·Chemical Society Reviews·S A IqbalM J Ingleson
May 16, 2020·Angewandte Chemie·Palas Baran PatiYoung S Park
Feb 6, 2021·Chemical Communications : Chem Comm·Merian CrumbachHolger Helten
May 24, 2019·Journal of the American Chemical Society·Jeffrey M FarrellFrank Würthner

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Methods Mentioned

BETA
NMR
X‐ray

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