Journal
ORGANIC LETTERS
Volume 19, Issue 21, Pages 5944-5947Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.7b02936
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Funding
- ERATO from JST
- JSPS KAKENHI [JP 26288014]
- Grants-in-Aid for Scientific Research [17H06442, 26288014, 17H03016] Funding Source: KAKEN
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An iridium-catalyzed ortho-selective C-H borylation of phenol and aniline derivatives has been successfully developed. Iridium/bipyridine-catalyzed C-H borylation generally occurred at the meta- and para-positions of aromatic substrates. Introduction of an electron withdrawing substituent on the bipyridine-type ligand and a methylthiomethyl group on the hydroxy and amino groups of the phenol and aniline substrates, however, dramatically altered the regioselectivity, affording exclusively ortho-borylated products. The reaction proceeded in good to excellent yields with, good functional group tolerance. C-H borylation was applied to the synthesis of a calcium receptor modulator.
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