Filling the Gaps in the Challenging AsymmetricHydroboration of 1,1-Disubstituted Alkenes with Simple Phosphite-Based Phosphinooxazoline Iridium Catalysts

Montserrat Diéguez Maria Biosca Marc Magre Oscar Pàmies

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TITLE:

Filling the Gaps in the Challenging AsymmetricHydroboration of 1,1-Disubstituted Alkenes with Simple Phosphite-Based Phosphinooxazoline Iridium Catalysts - PC:1257

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https://hdl.handle.net/20.500.11797/PC1257

URV's Author/s:	DIÉGUEZ FERNÁNDEZ, MONTSERRAT Maria Biosca Marc Magre PAMIES OLLÉ, OSCAR
Author, as appears in the article.:	Montserrat Diéguez Maria Biosca Marc Magre Oscar Pàmies
Author identifier:	0000-0002-8450-0656 n/a n/a 0000-0002-2352-8508
Journal publication year:	2014
Publication Type:	Post-print
ISSN:	1867-3880
Abstract:	We have identified a readily accessible phosphinooxazoline based phosphite-oxazoline catalytic system, (S)-4-isopropyl-2-{2-[(3,3¿,5,5¿-tetra-tert-butyl-1,1¿-biphenyl-2,2¿-diyl)phosphite]-phenyl}-2-oxazoline (L1 a), that can hydroborate a range of 1,1-disubstituted aryl olefins with high enantioselectivity (up to 94%), excellent yields and perfect regioselectivity. The new phosphite-oxazoline ligands efficiently hydroborate a broader range of olefins than previous phosphinooxazoline ligands. In particular, a wide range of a-tert-butylstyrenes can be hydroborated that bear aryl substituents with different electronic and steric properties, which complements previous results with N-heterocyclic copper catalysts, the only other system reported to date that has achieved these reactions.
Article's DOI:	10.1002/cctc.201402822
Link to the original source:	https://chemistry-europe.onlinelibrary.wiley.com/doi/epdf/10.1002/cctc.201402822
Papper version:	info:eu-repo/semantics/acceptedVersion
licence for use:	https://creativecommons.org/licenses/by/3.0/es/
Department:	Química Física i Inorgànica
Research group:	Organometàl.lics i Catàlisi Homogènia
Licence document URL:	https://repositori.urv.cat/ca/proteccio-de-dades/
Thematic Areas:	Chemistry
Keywords:	asymmetric catalysis
Entity:	Universitat Rovira i Virgili
Record's date:	2015-11-26
First page:	114
Last page:	120
Journal volume:	7

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Description:	We have identified a readily accessible phosphinooxazoline based phosphite-oxazoline catalytic system, (S)-4-isopropyl-2-{2-[(3,3¿,5,5¿-tetra-tert-butyl-1,1¿-biphenyl-2,2¿-diyl)phosphite]-phenyl}-2-oxazoline (L1 a), that can hydroborate a range of 1,1-disubstituted aryl olefins with high enantioselectivity (up to 94%), excellent yields and perfect regioselectivity. The new phosphite-oxazoline ligands efficiently hydroborate a broader range of olefins than previous phosphinooxazoline ligands. In particular, a wide range of a-tert-butylstyrenes can be hydroborated that bear aryl substituents with different electronic and steric properties, which complements previous results with N-heterocyclic copper catalysts, the only other system reported to date that has achieved these reactions.
Coverage:	Anglès
Type:	Post-print Post-print info:eu-repo/semantics/acceptedVersion
Contributor:	Organometàl.lics i Catàlisi Homogènia Química Física i Inorgànica Universitat Rovira i Virgili
Títol:	Filling the Gaps in the Challenging AsymmetricHydroboration of 1,1-Disubstituted Alkenes with Simple Phosphite-Based Phosphinooxazoline Iridium Catalysts
Subject:	Catàlisi asimètrica asymmetric catalysis Chemistry Química Química 1867-3880
Date:	2014
Format:	317 kb
Creator:	Montserrat Diéguez Maria Biosca Marc Magre Oscar Pàmies
Rights:	info:eu-repo/semantics/openAccess

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