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Volumn 15, Issue 38, 2009, Pages 9655-9659

Synthesis of C1-symmetric BINOLs employing N-heterocyclic carbene copper complexes

Author keywords

Asymmetric catalysis; Binaphthols; Carbenes; Copper; Oxidative coupling

Indexed keywords

2-NAPHTHOLS; ASYMMETRIC CATALYSIS; BINAPHTHOLS; CARBENES; COPPER COMPLEXES; CU COMPLEXES; ELECTRON-DEFICIENT; ELECTRON-RICH; GOOD YIELD; N-HETEROCYCLIC CARBENES; OXIDATIVE COUPLINGS; PRODUCT YIELDS;

EID: 70450181462     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200901295     Document Type: Article
Times cited : (26)

References (68)
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    • The use of the free carboxylic acid of the methyl ester 4 a gave low yields of the coupling product (<10%), and the starting material could be recovered in>80% yield. Oxidative coupling with electron-rich substrates such as 2-naphthol, 3-phenanthrol, 9-phenanthrol, and 2-aminonaphthalene gave approximately 5-15% yield in all cases. Oxidation of electron-rich 2-naphthols to highly polar and colored byproducts was observed. For more details on possible oxidation products and their influence in oxidative coupling reactions
    • The use of the free carboxylic acid of the methyl ester 4 a gave low yields of the coupling product (<10%), and the starting material could be recovered in>80% yield. Oxidative coupling with electron-rich substrates such as 2-naphthol, 3-phenanthrol, 9-phenanthrol, and 2-aminonaphthalene gave approximately 5-15% yield in all cases. Oxidation of electron-rich 2-naphthols to highly polar and colored byproducts was observed. For more details on possible oxidation products and their influence in oxidative coupling reactions, see: J. B. Hewgley, S.S. Stahl, M. C. Kozlowski, J. Am. Chem. Soc. 2008, 130, 12232-12233.
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    • See the Supporting Information for more information.
    • See the Supporting Information for more information.
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    • note
    • It was shown that it was necessary to have the ester in the 3-position for efficient coupling to occur because the reaction between 4a and 6i did not afford a mixed coupling product. In addition, 6i was reluctant to undergo homocoupling but could be reisolated in high yields, suggesting that the ester substituent in the 6-position is sufficiently electron-withdrawing to minimize the oxidation of 6i to unwanted byproducts. .


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.