Dehydroborylation of Terminal Alkynes Using Lithium Aminoborohydrides
Dehydrogenative borylation of terminal alkynes has recently emerged as an atom-economical one-step alternative to traditional alkyne borylation methodologies. Using lithium aminoborohydrides, formed in situ from the corresponding amine-boranes and <i>n</i>-butyllithium, a variety of arom...
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| Format: | Article |
| Language: | English |
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MDPI AG
2023-04-01
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| Series: | Molecules |
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| Online Access: | https://www.mdpi.com/1420-3049/28/8/3433 |
| _version_ | 1827744200354955264 |
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| author | P. Veeraraghavan Ramachandran Henry J. Hamann |
| author_facet | P. Veeraraghavan Ramachandran Henry J. Hamann |
| author_sort | P. Veeraraghavan Ramachandran |
| collection | DOAJ |
| description | Dehydrogenative borylation of terminal alkynes has recently emerged as an atom-economical one-step alternative to traditional alkyne borylation methodologies. Using lithium aminoborohydrides, formed in situ from the corresponding amine-boranes and <i>n</i>-butyllithium, a variety of aromatic and aliphatic terminal alkyne substrates were successfully borylated in high yield. The potential to form mono-, di-, and tri-<i>B</i>-alkynylated products has been shown, though the mono-product is primarily generated using the presented condition. The reaction has been demonstrated at large (up to 50 mmol) scale, and the products are stable to column chromatography as well as acidic and basic aqueous conditions. Alternately, the dehydroborylation can be achieved by treating alkynyllithiums with amine-boranes. In that respect, aldehydes can act as starting materials by conversion to the 1,1-dibromoolefin and in situ rearrangement to the lithium acetylide. |
| first_indexed | 2024-03-11T04:41:16Z |
| format | Article |
| id | doaj.art-322ddd9948dd4e0eb6c1835d31d152cb |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-03-11T04:41:16Z |
| publishDate | 2023-04-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-322ddd9948dd4e0eb6c1835d31d152cb2023-11-17T20:38:57ZengMDPI AGMolecules1420-30492023-04-01288343310.3390/molecules28083433Dehydroborylation of Terminal Alkynes Using Lithium AminoborohydridesP. Veeraraghavan Ramachandran0Henry J. Hamann1Herbert C. Brown Center for Borane Research, Department of Chemistry, Purdue University, 560 Oval Drive, West Lafayette, IN 47907, USAHerbert C. Brown Center for Borane Research, Department of Chemistry, Purdue University, 560 Oval Drive, West Lafayette, IN 47907, USADehydrogenative borylation of terminal alkynes has recently emerged as an atom-economical one-step alternative to traditional alkyne borylation methodologies. Using lithium aminoborohydrides, formed in situ from the corresponding amine-boranes and <i>n</i>-butyllithium, a variety of aromatic and aliphatic terminal alkyne substrates were successfully borylated in high yield. The potential to form mono-, di-, and tri-<i>B</i>-alkynylated products has been shown, though the mono-product is primarily generated using the presented condition. The reaction has been demonstrated at large (up to 50 mmol) scale, and the products are stable to column chromatography as well as acidic and basic aqueous conditions. Alternately, the dehydroborylation can be achieved by treating alkynyllithiums with amine-boranes. In that respect, aldehydes can act as starting materials by conversion to the 1,1-dibromoolefin and in situ rearrangement to the lithium acetylide.https://www.mdpi.com/1420-3049/28/8/3433amine-boranedehydrogenative borylationlithium aminoborohydridesalkynylborane-amines1,1-dibromoolefin |
| spellingShingle | P. Veeraraghavan Ramachandran Henry J. Hamann Dehydroborylation of Terminal Alkynes Using Lithium Aminoborohydrides Molecules amine-borane dehydrogenative borylation lithium aminoborohydrides alkynylborane-amines 1,1-dibromoolefin |
| title | Dehydroborylation of Terminal Alkynes Using Lithium Aminoborohydrides |
| title_full | Dehydroborylation of Terminal Alkynes Using Lithium Aminoborohydrides |
| title_fullStr | Dehydroborylation of Terminal Alkynes Using Lithium Aminoborohydrides |
| title_full_unstemmed | Dehydroborylation of Terminal Alkynes Using Lithium Aminoborohydrides |
| title_short | Dehydroborylation of Terminal Alkynes Using Lithium Aminoborohydrides |
| title_sort | dehydroborylation of terminal alkynes using lithium aminoborohydrides |
| topic | amine-borane dehydrogenative borylation lithium aminoborohydrides alkynylborane-amines 1,1-dibromoolefin |
| url | https://www.mdpi.com/1420-3049/28/8/3433 |
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