Iridium-Catalyzed Cage B(4)-Amidation Reaction of o -Carboranes with Dioxazolones: Selective Synthesis of Amidated o -Carboranes and Amidated and Methoxycarbonylated nido -Carboranes

Described is the Ir-catalyzed cage B(4)-amidation of -carboranes with dioxazolones by carboxylic acid-assisted B(4)-H bond activation under extremely mild conditions, affording amidated -carboranes and amidated and methoxycarbonylated -carboranes through sequential B(4)-amidation, O-methylation, and...

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Published inOrganic letters Vol. 23; no. 2; pp. 416 - 420
Main Authors Han, Gi Uk, Baek, Yonghyeon, Lee, Kyungsup, Shin, Seohyun, Chan Noh, Hee, Lee, Phil Ho
Format Journal Article
LanguageEnglish
Published United States 15.01.2021
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Summary:Described is the Ir-catalyzed cage B(4)-amidation of -carboranes with dioxazolones by carboxylic acid-assisted B(4)-H bond activation under extremely mild conditions, affording amidated -carboranes and amidated and methoxycarbonylated -carboranes through sequential B(4)-amidation, O-methylation, and B(3)-deboronation in one pot. Carboxylic acid used as a directing group after the cage B(4)-amidation is efficiently trapped by trimethylsilyldiazomethane instead of undergoing decarboxylation. Mechanism studies demonstrated that the O-methylation through trapping of acid occurred first, followed by the B(3)-deboronation.
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content type line 23
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.0c03927