期刊
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
卷 134, 期 17, 页码 7313-7316出版社
AMER CHEMICAL SOC
DOI: 10.1021/ja3023972
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资金
- Pennsylvania State University
- NSF [CAREER CHE-1055795]
- Division Of Chemistry
- Direct For Mathematical & Physical Scien [1055795] Funding Source: National Science Foundation
We report the efficient synthesis of alkyl ethers by the functionalization of unactivated sp(3)- and sp(2)- hybridized C H bonds. In the Pd(OAc)(2)-catalyzed, PhI(OAc)(2)-mediated reaction system, picolinamide-protected amine substrates undergo facile alkoxylation at the gamma or delta positions with a range of alcohols, including t-BuOH, to give alkoxylated products. This method features a relatively broad substrate scope for amines and alcohols, inexpensive reagents, and convenient operating conditions. This method highlights the emerging value of unactivated C-H bonds, particularly the C(sp(3))-H bond of methyl groups, as functional groups in organic synthesis.
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