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Generation of an N→B Ladder‐type Structure by Regioselective Hydroboration of an Alkenyl‐Functionalized Quaterpyridine
Author(s) -
Grandl Markus,
Sun Yu,
Pammer Frank
Publication year - 2016
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201600228
Subject(s) - hydroboration , regioselectivity , borane , chemistry , intramolecular force , conjugated system , boron , nonane , stereochemistry , substrate (aquarium) , reagent , combinatorial chemistry , organic chemistry , catalysis , oceanography , geology , polymer
An unusual reactivity of 2‐(1‐alkenyl)‐pyridines towards hydroboration with 9 H ‐borabicyclo[3.3.1]nonane (9 H ‐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.