English   español  
Please use this identifier to cite or link to this item: http://hdl.handle.net/10261/96613
logo share SHARE logo core CORE   Add this article to your Mendeley library MendeleyBASE

Visualizar otros formatos: MARC | Dublin Core | RDF | ORE | MODS | METS | DIDL
Exportar a otros formatos:

Phosphino hydrazones as suitable ligands in the asymmetric Suzuki-Miyaura cross-coupling

AuthorsRos, Abel ; Estepa, Beatriz; Bermejo, Antonio; Álvarez, Eleuterio ; Fernández, Rosario; Lassaletta, José M.
Issue Date2012
PublisherAmerican Chemical Society
CitationJournal of Organic Chemistry 77: 4740- 4750 (2012)
AbstractPhosphino hydrazones derived from C 2-symmetric hydrazines exhibit excellent catalytic activity and provide good enantioselectivities in the asymmetric Suzuki-Miyaura cross-coupling to axially chiral biaryls, in particular for the most challenging reactions of monocyclic, functionalized aryl bromides and triflates. X-ray analysis of preformed [Pd(P/N)Cl 2] precatalysts [(P/N) = phosphino hydrazone] revealed a strong n-π conjugation in the hydrazone moiety, identified by a high planarity degree at the pyrrolidine N(sp 3) atom, that makes rotations around N-N bonds inconsequential. The complexes are also characterized by an envelope-like conformation with the Pd atom placed at the opposite side to the 2-phenyl group on the nearest stereogenic center of the pyrrolidine group. The isolation and structural analysis of oxidative addition intermediates indicate that the configurational stability of Pd-C(Ar) bonds is dependent on the substitution pattern in the aryl bromide. © 2012 American Chemical Society.
Identifiersdoi: 10.1021/jo300548z
issn: 0022-3263
Appears in Collections:(IIQ) Artículos
Files in This Item:
File Description SizeFormat 
accesoRestringido.pdf15,38 kBAdobe PDFThumbnail
Show full item record
Review this work

Related articles:

WARNING: Items in Digital.CSIC are protected by copyright, with all rights reserved, unless otherwise indicated.