In:
New Journal of Chemistry, Royal Society of Chemistry (RSC), Vol. 46, No. 4 ( 2022), p. 1751-1762
Abstract:
A series of diamidophosphite ligands of various structures and denticities were synthesized from (11 S ,12 S )-bis(hydroxymethyl)-9,10-dihydro-9,10-ethanoanthracene as a “roof shaped” 1,4-diol. On the basis of these ligands, we obtained three types of Pd(II) allylic complexes: a P , P -chelate, a P,S -bridged head-to-tail dinuclear complex, and complexes each containing a pair of P -monodentately coordinated P -, P , N - or P , S -ligands. The structures of the ligands and their complexes were determined using 2D NMR spectroscopy. Four diamidophosphites were also characterized via their X-ray structural data. This kind of stereoselector exhibited up to 98% ee in the Pd-mediated allylic substitution of ( E )-1,3-diphenylallyl acetate with C- and N-nucleophiles. In the Pd-catalyzed allylic alkylation of cinnamyl acetate with various C-nucleophiles, ee values of up to 90% were obtained. In addition, up to 71% ee was achieved in the Pd-catalyzed asymmetric amination of 2-(diethoxyphosphoryl)-1-phenylallyl acetate with aniline, which is a pioneering example of diamidophosphite-type ligand involvement in this challenging reaction. The effects of the diamidophosphite moiety and the denticity of the ligands on the catalytic activity and enantioselectivity were investigated.
Type of Medium:
Online Resource
ISSN:
1144-0546
,
1369-9261
Language:
English
Publisher:
Royal Society of Chemistry (RSC)
Publication Date:
2022
detail.hit.zdb_id:
1472933-7
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