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Copper-Catalyzed Triboration of Terminal Alkynes Using B\(_2\)pin\(_2\): Efficient Synthesis of 1,1,2-Triborylalkenes
Please always quote using this URN: urn:nbn:de:bvb:20-opus-206694
- 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.…
Author: | Xiaocui Liu, Wenbo Ming, Alexandra Friedrich, Florian Kerner, Todd B. Marder |
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URN: | urn:nbn:de:bvb:20-opus-206694 |
Document Type: | Journal article |
Faculties: | Fakultät für Chemie und Pharmazie / Institut für Anorganische Chemie |
Language: | English |
Parent Title (English): | Angewandte Chemie International Edition |
Year of Completion: | 2020 |
Volume: | 59 |
Issue: | 1 |
Pagenumber: | 304-309 |
Source: | Angewandte Chemie International Edition 2020, 59, 304–309. DOI: 10.1002/anie.201908466 |
DOI: | https://doi.org/10.1002/anie.201908466 |
Dewey Decimal Classification: | 5 Naturwissenschaften und Mathematik / 54 Chemie / 546 Anorganische Chemie |
Tag: | boronate esters; borylation; cross-coupling; diboration; halogenation |
Release Date: | 2020/09/21 |
Licence (German): | CC BY-NC: Creative-Commons-Lizenz: Namensnennung, Nicht kommerziell 4.0 International |