Study on the synthesis of nonracemic C2-symmetric 1,1′-binaphthyl-2,2′-diyl bridged ferrocene. Stereochemical result of the cross-coupling reactions controlled by Pd(II) or Pd(IV) complex intermediacy

Recent applications of the Suzuki–Miyaura cross-coupling reaction in organic synthesis

“…169 They also found a hydrodehalogenated product 130 from the corresponding dihalide 127 and oligomers of the coupling product when a C 2 -symmetric palladacycle complex was used as the catalyst. Other reactions such as Negishi and Stille couplings gave the corresponding non-racemic products.…”

1,1′‐Diborylferrocenes from [2]Boraferrocenophanes by Boron–Boron Exchange

“…of HBPin (6) in heptanes under refluxing conditions for 2 h. Interestingly, this also results in the formation of 5 albeit in significantly lower yield of only 35 %, as indicated by the aforementioned characteristic 1 H NMR and 11 B NMR spectroscopic data. Thus, an alternative access to 5 is provided in addition to common condensation routes [15][16][17] and the recently developed protocol employing 4 and various ferrocenes in the presence of a suitable Ir catalyst. [18] Additionally, it was investigated whether this reaction is restricted to pinacolatoboranes or displays a somewhat wider applicability.…”

Chiral Binaphthalenes Bearing Two Pyridine Ligands Attached Via Acetylene Spacers. Synthesis and Coordination Study

“…Substitution reactions, in particular cross-coupling reactions, at both positions 2 and 2′ are critical for conservation of stereochemical information in the course of preparation of such derivatives [4][5][6][7] . Specialty of the cross-coupling reactions (or any substitutions) at the positions 2 and 2′ consist in substan-…”

“…tial steric hindrance (bulky 2-substituted 1-naphthyl group in the position adjacent to the reaction center) and the risk of racemization during the reaction, since these reactions take place in the positions where mutual nonbonding interactions between groups (replaced in the course of the reaction) is decisive for configurational stability of these derivatives [5][6][7] .…”

“…Being encouraged by the efficient Negishi 2,2′-dialkylation 5 and diarylation 6,16 of 2,2′-disubstituted 1,1′-binaphtha-lenes, in particular diiodide 10, we concentrated our effort on the use of cross-coupling reactions.…”