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Title

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.
URIhttp://hdl.handle.net/10261/96613
DOI10.1021/jo300548z
Identifiersdoi: 10.1021/jo300548z
issn: 0022-3263
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