Copper-Catalyzed Triboration of Terminal Alkynes Using B\(_2\)pin\(_2\): Efficient Synthesis of 1,1,2-Triborylalkenes
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- We report herein the catalytic triboration of terminal alkynes with B\(_2\)pin\(_2\) (bis(pinacolato)diboron) using readily available Cu(OAc)\(_2\) and P\(^n\)Bu\(_3\). Various 1,1,2‐triborylalkenes, a class of compounds that have been demonstrated to be potential matrix metalloproteinase (MMP‐2) inhibitors, were obtained directly in moderate to good yields. The process features mild reaction conditions, a broad substrate scope, and good functional group tolerance. This copper‐catalyzed reaction can be conducted on a gram scale to produce theWe report herein the catalytic triboration of terminal alkynes with B\(_2\)pin\(_2\) (bis(pinacolato)diboron) using readily available Cu(OAc)\(_2\) and P\(^n\)Bu\(_3\). Various 1,1,2‐triborylalkenes, a class of compounds that have been demonstrated to be potential matrix metalloproteinase (MMP‐2) inhibitors, were obtained directly in moderate to good yields. The process features mild reaction conditions, a broad substrate scope, and good functional group tolerance. This copper‐catalyzed reaction can be conducted on a gram scale to produce the corresponding 1,1,2‐triborylalkenes in modest yields. The utility of these products was demonstrated by further transformations of the C−B bonds to prepare gem ‐dihaloborylalkenes (F, Cl, Br), monohaloborylalkenes (Cl, Br), and trans ‐diaryldiborylalkenes, which serve as important synthons and have previously been challenging to prepare.…
Autor(en): | Xiaocui Liu, Wenbo Ming, Alexandra Friedrich, Florian Kerner, Todd B. Marder |
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URN: | urn:nbn:de:bvb:20-opus-206694 |
Dokumentart: | Artikel / Aufsatz in einer Zeitschrift |
Institute der Universität: | Fakultät für Chemie und Pharmazie / Institut für Anorganische Chemie |
Sprache der Veröffentlichung: | Englisch |
Titel des übergeordneten Werkes / der Zeitschrift (Englisch): | Angewandte Chemie International Edition |
Erscheinungsjahr: | 2020 |
Band / Jahrgang: | 59 |
Heft / Ausgabe: | 1 |
Seitenangabe: | 304-309 |
Originalveröffentlichung / Quelle: | Angewandte Chemie International Edition 2020, 59, 304–309. DOI: 10.1002/anie.201908466 |
DOI: | https://doi.org/10.1002/anie.201908466 |
Allgemeine fachliche Zuordnung (DDC-Klassifikation): | 5 Naturwissenschaften und Mathematik / 54 Chemie / 546 Anorganische Chemie |
Freie Schlagwort(e): | boronate esters; borylation; cross-coupling; diboration; halogenation |
Datum der Freischaltung: | 21.09.2020 |
Lizenz (Deutsch): | CC BY-NC: Creative-Commons-Lizenz: Namensnennung, Nicht kommerziell 4.0 International |