Photoswitching of the Lewis Acidity of a Catecholborane Bearing an Azo Group Based on the Change in Coordination Number of Boron
- 11 August 2005
- journal article
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 7 (18), 3909-3911
- https://doi.org/10.1021/ol051337e
Abstract
Photoisomerization of a catecholborane bearing a 2-(phenylazo)phenyl group with an N-B dative bond caused photoswitching of the coordination number of boron between 3 and 4. The Lewis acidity of the catecholborane was switched by photoirradiation, and the complexation ability of the (E)- and the (Z)-isomers of the catecholborane with pyridine differs by more than a factor of 300. [reaction: see text]Keywords
This publication has 18 references indexed in Scilit:
- Synthesis of a Novel Potential Tridentate Anthracene Ligand, 1,8-Bis(dimethylamino)-9-bromoanthracene, and Its Application as Chelate Ligand for Synthesis of the Corresponding Boron and Palladium CompoundsChemistry – A European Journal, 2002
- pKa Values and Geometries of Secondary and Tertiary Amines Complexed to Boronic AcidsImplications for Sensor DesignOrganic Letters, 2001
- Crystallization-Induced Asymmetric Transformation vs Quasi-Racemate Formation in Tetravalent Boron ComplexesJournal of the American Chemical Society, 2000
- Effect of Benzylic Methyl Groups on Kinetic Basicity of Amine Ligand in o-Boron Substituted N,N-DimethylbenzylaminesBulletin of the Chemical Society of Japan, 1999
- Arylboron Compounds as Acid Catalysts in Organic Synthetic TransformationsEuropean Journal of Organic Chemistry, 1999
- An intramolecularly stabilized arylboron dibromideHeteroatom Chemistry, 1998
- Synthesis and structural investigation of two potential boronate affinity chromatography ligands catechol [2-(diisopropylamino)carbonyl]phenylboronate and catechol [2-(diethylamino)carbonyl, 4-methyl]phenylboronateJournal of Organometallic Chemistry, 1995
- Synthesis of 8-substituted 1-naphthylamine derivatives. exceptional reactivity of the substituents.Tetrahedron, 1988
- Zur Chemie von Haftgruppen, IV. Über eine außerordentliche Erhöhung der Reaktivität von Arylboronsäuren durch NachbargruppenEuropean Journal of Inorganic Chemistry, 1985
- Arylboronic acids with intramolecular B–N interaction: convenient synthesis through ortho-lithiation of substituted benzylaminesJournal of Organometallic Chemistry, 1983