Nickel-Catalyzed Ring-Opening C–O Functionalization of peri-Xanthenoxanthenes for 8-Substituted Binaphthol Synthesis

Autor:	Toshiyuki Kamei, Toyoshi Shimada, Naoto Minamino, Naoki Matsuyama
Rok vydání:	2021
Předmět:	Nickel chemistry Ligand Reagent Organic Chemistry Polymer chemistry chemistry.chemical_element Surface modification Physical and Theoretical Chemistry Ring (chemistry) Biochemistry Catalysis
Zdroj:	Organic Letters. 23:3908-3912
ISSN:	1523-7052 1523-7060
DOI:	10.1021/acs.orglett.1c01053
Popis:	Herein, we disclose the Ni-catalyzed ring-opening C-O functionalization of peri-xanthenoxanthenes using Grignard reagents that forms 8-monofunctionalized binaphthols. 1,2-Bis(dicyclohexylphosphino)ethane was the best ligand for alkylations and ICy for arylation. After mechanistic investigations, we assumed that the reaction proceeds via C-O reduction and subsequent C-O functionalization. To verify the mechanism, the intermediate after reduction was isolated. Moreover, the asymmetric addition, using 8-octylbinaphthol after optical resolution, was studied.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::6c29a649efe743304dcbe80561cfa7f9 https://doi.org/10.1021/acs.orglett.1c01053 Zobrazit plný text záznamu