Journal
ORGANIC LETTERS
Volume 19, Issue 13, Pages 3450-3453Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.7b01423
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Funding
- JSPS KAKENHI [JP 26288014]
- CREST from JST
- Grants-in-Aid for Scientific Research [26288014, 17H03016] Funding Source: KAKEN
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Treatment of 2-phenylpyridines (or their analogs) with a 9-bicycloboranonane dimer (9-BBN dimer) in the presence of a catalytic amount of a commercially available iron salt, FeBr3, gave ortho-borylated products in moderate to excellent yields with good functional group tolerance. The reaction proceeded in good yield, even in gram-scale, and also occurred at the C-H bond of heteroaromatic compounds. The cost of the C-H borylation is dramatically lower than that of a previously reported similar palladium-catalyzed reaction. The products exhibit an intramolecular B-N Lewis acid-base interaction and fluoresce in both solution and solid states due to their electron push-pull structures.
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