Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 137, Issue 4, Pages 1593-1600Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ja511622e
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Funding
- MEXT, Japan
- ACT-C from JST, Japan
- JSPS
- Grants-in-Aid for Scientific Research [22105002, 13J00827] Funding Source: KAKEN
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The rhodium-catalyzed reaction of aryl 2-pyridyl ethers with a diboron reagent results in the formation of arylboronic acid derivatives via activation of the C(aryl)-O bonds. The straightforward synthesis of 1,2-disubstituted arenes was enabled through catalytic ortho C-H bond functionalization directed by the 2-pyridyloxy group followed by substitution of this group with a boryl group. Several control experiments revealed that the presence of a sp2 nitrogen atom at the 2-position of the substrate and the use of a boron-based reagent were crucial for the activation of the relatively inert C(aryl)-O bond of aryl 2-pyridyl ethers.
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