期刊
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
卷 131, 期 50, 页码 18057-+出版社
AMER CHEMICAL SOC
DOI: 10.1021/ja906514s
关键词
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资金
- National Institutes of Health [GM-079339]
- Bristol Myers Squibb
The formation of ethers by C-O bond formation under harsh basic or acidic conditions is an entrenched synthetic disconnection in organic chemistry. We report a strategic alternative that involves the BF3 center dot OEt2-promoted coupling of stable, easily prepared acetals with widely available potassium aryl-, alkenyl-, and alkynyltrifluoroborates. This fast, operationally simple process offers straightforward access to dialkyl ethers, many of which would be difficult to prepare using classical methods. The use of MOM-protected alcohols and acetal-protected aldehydes enables ether formation without recourse to protecting-group manipulations or strong bases.
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