Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 135, Issue 30, Pages 10978-10981Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ja405925w
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Funding
- Fonds der Chemischen Industrie
- Studienstiftung des deutschen Volkes
- Deutsche Forschungsgemeinschaft (International Research Training Group Munster-Nagoya) [GRK 1143]
- Einstein Foundation (Berlin)
- Grants-in-Aid for Scientific Research [25109522, 23000007, 23685015, 25105725] Funding Source: KAKEN
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The B-H bond of typical boranes is heterolytically split by the polar Ru-S bond of a tethered ruthenium(II) thiolate complex, affording a ruthenium(II) hydride and borenium ions with a dative interaction with the sulfur atom. These stable adducts were spectroscopically characterized, and in one case, the B-H bond activation step was crystallographically verified, a snapshot of the sigma-bond metathesis. The borenium ions derived from 9-borabicyclo[3.3.1]nonane dimer [(9-BBN)(2)], pinacolborane (pinBH), and catecholborane (catBH) allowed for electrophilic aromatic substitution of indoles. The unprecedented electrophilic borylation with the pinB cation was further elaborated for various nitrogen heterocycles.
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