Generation of an N→B Ladder‐type Structure by Regioselective Hydroboration of an Alkenyl‐Functionalized Quaterpyridine |
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| Authors: | Markus Grandl Dr. Yu Sun Dr. Frank Pammer |
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| Affiliation: | 1. Institute of Organic Chemistry II and Advanced Materials, University of Ulm, Ulm, Germany;2. Fachbereich Chemie, Technische Universit?t Kaiserslautern, Kaiserslautern, Germany |
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| Abstract: | An unusual reactivity of 2‐(1‐alkenyl)‐pyridines towards hydroboration with 9H‐borabicyclo[3.3.1]nonane (9H‐BBN) has been employed to selectively introduce two borane groups into a conjugated quaterpyridine. Quantitative conversion of the substrate was observed with exclusive regioselectivity. A molecular structure that allows intramolecular N→B coordination was generated. The effect of the ladder formation on the molecular structure and the electronic properties of the conjugated system have been investigated. The synthetic strategy demonstrated herein offers a facile access to N→B ladder‐type structures from readily available substrates, and allows to simultaneously introduce several boron centers under mild conditions. |
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| Keywords: | aromatic compounds electronic structure heterocyclic compounds hydroboration regioselectivity |
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