Boroxine template for macrocyclization and postfunctionalization

A novel synthetic strategy for large macrocyclic molecules using boroxine formation was developed. For this, the threefold intramolecular olefin metathesis of 3,5-bis(alkenyloxy)phenylboroxines with various lengths of alkenyl chains, formed by the dehydration of the corresponding boronic acid substr...

Full description

Saved in:
Bibliographic Details
Published in:Chemical communications (Cambridge, England) England), 2022-11, Vol.58 (9), p.12544-12547
Main Authors: Ono, Kosuke, Onodera, Satoru, Kawai, Hidetoshi
Format: Article
Language:English
Subjects:
Dehydration
Macrocyclic compounds
Metathesis
Substrates
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:A novel synthetic strategy for large macrocyclic molecules using boroxine formation was developed. For this, the threefold intramolecular olefin metathesis of 3,5-bis(alkenyloxy)phenylboroxines with various lengths of alkenyl chains, formed by the dehydration of the corresponding boronic acid substrates, together with treatment with pinacol, was used to produce 39-, 45-, and 51-membered macrocyclic compounds with three boronate units. The boroxine moiety functions as a covalent template but can also be used to postmodify the macrocycle. Boroxine-templated macrocyclization implemented in this way does not require the addition of template molecules and simplifies the synthetic procedure. Boroxine-templated macrocyclization: Olefin metathesis of boronic acid substrates in the presence of MS4A followed by workup with pinacol yields the desired macrocyclic compounds with modifiable three boron units.
ISSN:1359-7345
1364-548X
DOI:10.1039/d2cc04691a