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Expansion of the scope of alkylboryl-bridged N -> B-ladder boranes: new substituents and alternative substrates
Univ Ulm, Inst Organ Chem & Adv Mat 2, Albert Einstein Allee 11, D-89081 Ulm, Germany.ORCID iD: 0000-0002-3869-0196
Univ Ulm, Inst Organ Chem & Adv Mat 2, Albert Einstein Allee 11, D-89081 Ulm, Germany.
Univ Ulm, Inst Analyt & Bioanalyt Chem, Albert Einstein Allee 11, D-89081 Ulm, Germany.
Tech Univ Kaiserslautern, Fachbereich Chem, Erwin Schrodinger Str 54, D-67663 Kaiserslautern, Germany.
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2019 (English)In: Dalton Transactions, ISSN 1477-9226, E-ISSN 1477-9234, Vol. 48, no 27, p. 10298-10312Article in journal (Refereed) Published
Abstract [en]

A series of new boranes capable of forming intramolecular N -> B-heterocycles has been prepared and their properties have been studied by electrochemical methods and UV-vis-spectroscopy complemented by DFT calculations. A dimethylborane (BMe2), haloborane derivatives (BBr2, BF2, BI2) and mixed cyano/isocyano-borane (B(CN)(NC)) have been prepared by different techniques. Furthermore, 2 '-alkynyl-substituted 2-phenylpyridines bearing terminal tert-butyl- and trimethylsilyl-groups are introduced as a new class of substrates for hydroboration. Successful hydroboration with either 9H-borabicyclo[3.3.1]-nonane (9H-BBN), dimesitylborane (Mes(2)B-H), or Piers' borane ((C6F5)(2)B-H, BPF-H) furnished new pi-extended boranes capable of forming intramolecular six- or seven-membered N -> B-heterocycles (tBuBBN, SiBPF), and, in the case of Mes(2)BH, formation of a sterically crowded styrylborane (SiBMes(2)) incapable of intramolecular N -> B-coordination was observed. All the boranes listed above except BMe2 have been structurally characterized, and a study of their electrochemical properties showed that the systematic variation of the substituents on boron allows for the incremental variation of the electron affinity of the phenylpyridine-model system over a total range of >0.7 eV between alkylboranes (BMe2, BBN) and B(CN)(NC). B(CN)(NC) shows the strongest N -> B-bond (approximate to 175 kJ mol(-1)), and highest electron-affinity observed so far, and is the first example of a borane bearing an isocyano-substituent on boron.

Place, publisher, year, edition, pages
ROYAL SOC CHEMISTRY , 2019. Vol. 48, no 27, p. 10298-10312
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Organic Chemistry
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URN: urn:nbn:se:uu:diva-391376DOI: 10.1039/c9dt01555hISI: 000475742900042PubMedID: 31210241OAI: oai:DiVA.org:uu-391376DiVA, id: diva2:1348231
Available from: 2019-09-03 Created: 2019-09-03 Last updated: 2019-09-03Bibliographically approved

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Orthaber, Andreas

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