172297-36-8Relevant academic research and scientific papers
Synthesis of structurally diversified BINOLs and NOBINs via palladium-catalyzed C-H arylation with diazoquinones
Zhang, Ji-Wei,Jiang, Fei,Chen, Ye-Hui,Xiang, Shao-Hua,Tan, Bin
, p. 1515 - 1521 (2021/07/06)
Privileged biaryl frameworks, BINOL and NOBIN, were efficiently constructed with sole 1-DNQs as arylation reagents under one set of reaction conditions. The judicious selection of palladium-catalytic system plays a pivotal role in the excellent selectivities. This transformation accommodated fairly broad substrate generality for both 2-naphthol and N-Boc-2-naphthylamine and afforded the structurally diversified BINOLs and NOBIN derivatives in high efficiency. Notably, the bromo-substituents which cannot survive in conventional palladium-catalyzed reactions were well-compatible with this set of conditions, providing an effective handle for further enriching the library of BINOLs and NOBINs. Preliminary attempts on the asymmetric variant of this reaction were also performed with up to 80:20 er for BINOLs synthesis. [Figure not available: see fulltext.].
Nucleophilic coupling of alkali 2-naphthoxides with 1-bromo-2-naphthols. Ion-pairing and halogen dance in the formation of 1,1'-binaphthalene-2,2'-diols
Belohradsky, Martin,Holy, Petr,Zavada, Jiri
, p. 1853 - 1856 (2007/10/02)
A very pronounced effect of solvent and cation has been found in the investigated reaction, indicating that ion-pairing is indispensable in the product formation.A simple rationale has been provided assuming self-assembly of the complementary reactants driven by hydrogen bonding and ion-pairing interactions.Concomitantly, halogen exchange between the reaction partners has been demonstrated to be a concurrent pathway, resulting from the nucleophilic 2-napthoxide attack at the bromide terminus of the Cα-Br bond in the participating 1-bromo-2-naphthol.
