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Volumn 14, Issue 5, 2008, Pages 1518-1523

Water compatible gold(III)-catalysed synthesis of unsymmetrical ethers from alcohols

Author keywords

Alcohols; Carbocations; Gold; Homogeneous catalysis; Lewis acids

Indexed keywords

ETHERS; GOLD COMPOUNDS; ORGANIC COMPOUNDS; STEEL BEAMS AND GIRDERS;

EID: 43549087678     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200701134     Document Type: Article
Times cited : (56)

References (32)
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    • The referees suggested that the HCl produced from the gold catalyst could be responsible for the observed etherification reaction. To assure that this possibility can be ruled out, several control experiments were performed. In general, much less efficient transformations were achieved when reactions were catalysed by 5% HCl. For instance, the reaction of 1 a with 2 f gave a mixture of unsymmetrical ether (35% yield; 72% under gold(III) catalysis) and symmetrical ether (14% yield, On the other hand, indanol 1b and isopropanol (2f) gave a mixture of unsymmetrical ether (45, and indene (28, elimination product, No reaction took place between tertiary alcohol 2 g and isopropanol (2f) with 5% HCl
    • The referees suggested that the HCl produced from the gold catalyst could be responsible for the observed etherification reaction. To assure that this possibility can be ruled out, several control experiments were performed. In general, much less efficient transformations were achieved when reactions were catalysed by 5% HCl. For instance, the reaction of 1 a with 2 f gave a mixture of unsymmetrical ether (35% yield; 72% under gold(III) catalysis) and symmetrical ether (14% yield). On the other hand, indanol 1b and isopropanol (2f) gave a mixture of unsymmetrical ether (45%) and indene (28%) (elimination product). No reaction took place between tertiary alcohol 2 g and isopropanol (2f) with 5% HCl.
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    • Angew. Chem. Int. Ed. 2005, 44, 3913-3917;
    • (2005) Angew. Chem. Int. Ed , vol.44 , pp. 3913-3917


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.