215433-53-7Relevant articles and documents
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.].
Double-Fold Ortho and Remote C-H Bond Activation/Borylation of BINOL: A Unified Strategy for Arylation of BINOL
Bisht, Ranjana,Chaturvedi, Jagriti,Pandey, Gajanan,Chattopadhyay, Buddhadeb
supporting information, p. 6476 - 6480 (2019/08/20)
A double-fold ortho and remote C-H borylation of BINOL is described. The proposed mechanisms involved electrostatically and sterically directed ortho and remote C-H activation processes, respectively. While B2eg2 (eg = ethylene glyco
Efficient synthesis of 3,3'-diaryl binaphthol through a one-step method
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Paragraph 0054-0056, (2018/07/30)
The invention relates to a class of catalysis reactions of binaphthol and halogenated aromatic hydrocarbons, particularly to efficient preparation of 3,3'-diaryl binaphthol and 3-Bulkyaryl binaphtholthrough a one-step method, and belongs to the technical field of asymmetric catalysis. A purpose of the present invention is to provide a simple and practical method for preparing 3,3'-diaryl binaphthol through a one-step reaction of inexpensive BINOL and a brominated aromatic hydrocarbon reagent, and is further to provide a simple and rapid method for conveniently preparing 3-aryl binaphthol withhigh steric hindrance.
Enantioenriched synthesis of C 1-symmetric BINOLs: Iron-catalyzed cross-coupling of 2-naphthols and some mechanistic insight
Egami, Hiromichi,Matsumoto, Kenji,Oguma, Takuya,Kunisu, Takashi,Katsuki, Tsutomu
supporting information; experimental part, p. 13633 - 13635 (2010/11/17)
Highly enantioselective aerobic oxidative cross-coupling of 2-naphthols with broad substrate scope was achieved using an iron(salan) complex as the catalyst. Enantiomeric excesses of the products ranged from 87 to 95%. The scope of the cross-coupling reac
Asymmetric allylboration of aldehydes and ketones using 3,3′-disubstitutedbinaphthol-modified boronates
Wu, T. Robert,Shen, Lixin,Chong, J. Michael
, p. 2701 - 2704 (2007/10/03)
Allylboronates derived from 3,3′-disubstituted 2,2′-binaphthols react with aldehydes and ketones to give the expected allylated products with up to >99:1 er. Highest selectivities were observed for aromatic ketones. The bis(trifluoromethyl) derivative is particularly outstanding in terms of reactivity, selectivity, and robustness.
Synthesis and application of macrocyclic binaphthyl ligands with extended chiral bias
Yan, Yuan-Yong,Widhalm, Michael
, p. 3607 - 3610 (2007/10/03)
Two macrocyclic and one non-cyclic chiral diphosphine ligand containing a 2,2'-bridged binaphthyl unit were synthesized in six steps from (R)-2,2'- dimethoxy-1,1'-binaphthyl in overall yields of 25 and 17%, respectively. The new ligands showed asymmetric inductions of up to 98% e.e. if used in palladium catalyzed allylic alkylation reactions.
