S 98 Synthesis of chiral ferrocenylazines. Negishi cross-coupling or S N H reactions? [Electronic resource] / A. A Musikhina, I. A. Utepova, N. S. Serebryakov, O. N. Chupakhin, V. N. Charushin // Russian Journal of Organic Chemistry (Translation of Zhurnal Organicheskoi Khimii). - 2013. - Vol.49, №8. - С. 1191-1194. - Bibliogr. : p. 1194 (28 ref.) Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): SYNTHESIS -- CHIRAL FERROCENYLAZINES -- NEGISHI Аннотация: Preparation of new hetaryl-containing planar chiral ferrocene by a nucleophilic substitution of hydrogen in azines was performed using a lithium derivative of (S)-ferrocenyl-p-tolylsulfoxide as s nucleophilic reagent \\\\expert2\\NBO\\Russian Journal of Organic Chemistry\\2013, 49, (8), 1191-1194.pdf |
T 98 Two Approaches in the Synthesis of Planar Chiral Azinylferrocenes [Electronic resource] / I. A. Utepova, O. N. Chupakhin, P. O. Serebrennikova, A. A Musikhina, V. N. Charushin // Journal of Organic Chemistry. - 2014. - Vol. 79, № 18. - С. 8659-8667. - Bibliogr. : p. 8666-8667 (34 ref.) Рубрики: ХИМИЧЕСКИЕ НАУКИ Кл.слова (ненормированные): CHIRAL AZINYLFERROCENES -- CROSS-COUPLING REACTION -- HALOGENATED AZINES Аннотация: Two synthetic routes to the chiral azinylferrocenes (CAFs) 5 and 15, key intermediates for the synthesis of new enantiomerically enriched P,N-ligands, have been compared. The first approach is based on the palladium-catalyzed cross-coupling reaction of halogenated azines with organozinc derivatives of ferrocenes (the Negishi reaction). The second approach exploits a new synthetic methodology, which provides a shorter pathway, through the direct C–H functionalization of aromatics by the C–C coupling of halogen-free (hetero)arenes with lithium ferrocenes bearing stereogenic C and S atoms. The palladium complexes of P,N-ligands have been used as catalysts for the Tsuji–Trost reaction, which proceeds with high enantioselectivity to give allylic substitution products in good yields. \\\\expert2\\nbo\\Journal of Organic Chemistry\\2014, v.79, p.8659.pdf |