Single-nitrogen atom incorporation into B=B bond via the N=N bond splitting of diazo compound and diazirine
Triboraazabutenyne 3 is synthesized by the reaction of diboraazabutenyne 1 with aryl boron dibromide followed by the reduction. The ligand exchange to replace phosphine on the terminal sp2 B atom with carbene furnishes 4. 11 B NMR, solid-state structures, and computational studies disclose that 3 an...
| Main Authors: | , |
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| Other Authors: | |
| Format: | Journal Article |
| Language: | English |
| Published: |
2023
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| Online Access: | https://hdl.handle.net/10356/171089 |
| _version_ | 1826112785268867072 |
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| author | Zhu, Lizhao Kinjo, Rei |
| author2 | School of Chemistry, Chemical Engineering and Biotechnology |
| author_facet | School of Chemistry, Chemical Engineering and Biotechnology Zhu, Lizhao Kinjo, Rei |
| author_sort | Zhu, Lizhao |
| collection | NTU |
| description | Triboraazabutenyne 3 is synthesized by the reaction of diboraazabutenyne 1 with aryl boron dibromide followed by the reduction. The ligand exchange to replace phosphine on the terminal sp2 B atom with carbene furnishes 4. 11 B NMR, solid-state structures, and computational studies disclose that 3 and 4 feature the extremely polarized B=B bond. 4 readily splits the N=N bond of both diazo compound and diazirine under ambient conditions, whereby one nitrogen atom is incorporated into the B=B moiety leading to a neutral diboraazaallene 6. The mechanism of the reaction between 4 and diazo compound is extensively investigated by density functional theory (DFT) calculations, as well as the isolation of an intermediate. |
| first_indexed | 2024-10-01T03:12:28Z |
| format | Journal Article |
| id | ntu-10356/171089 |
| institution | Nanyang Technological University |
| language | English |
| last_indexed | 2024-10-01T03:12:28Z |
| publishDate | 2023 |
| record_format | dspace |
| spelling | ntu-10356/1710892023-10-13T15:31:41Z Single-nitrogen atom incorporation into B=B bond via the N=N bond splitting of diazo compound and diazirine Zhu, Lizhao Kinjo, Rei School of Chemistry, Chemical Engineering and Biotechnology Science::Chemistry B-B Unsaturated Bond Bond Activation Triboraazabutenyne 3 is synthesized by the reaction of diboraazabutenyne 1 with aryl boron dibromide followed by the reduction. The ligand exchange to replace phosphine on the terminal sp2 B atom with carbene furnishes 4. 11 B NMR, solid-state structures, and computational studies disclose that 3 and 4 feature the extremely polarized B=B bond. 4 readily splits the N=N bond of both diazo compound and diazirine under ambient conditions, whereby one nitrogen atom is incorporated into the B=B moiety leading to a neutral diboraazaallene 6. The mechanism of the reaction between 4 and diazo compound is extensively investigated by density functional theory (DFT) calculations, as well as the isolation of an intermediate. National Research Foundation (NRF) Submitted/Accepted version We are grateful to Nanyang Technological University (NTU) and the National Research Foundation, Singapore (NRF-NRFI07-2021-0002) for financial support. 2023-10-12T13:06:56Z 2023-10-12T13:06:56Z 2023 Journal Article Zhu, L. & Kinjo, R. (2023). Single-nitrogen atom incorporation into B=B bond via the N=N bond splitting of diazo compound and diazirine. Angewandte Chemie International Edition, 62(33), e202306519-. https://dx.doi.org/10.1002/anie.202306519 1433-7851 https://hdl.handle.net/10356/171089 10.1002/anie.202306519 37409397 2-s2.0-85163954561 33 62 e202306519 en NRF-NRFI07-2021-0002 Angewandte Chemie International Edition © 2023 Wiley-VCHGmbH. All rights reserved. This article may be downloaded for personal use only. Any other use requires prior permission of the copyright holder. The Version of Record is available online at http://doi.org/10.1002/anie.202306519. application/pdf |
| spellingShingle | Science::Chemistry B-B Unsaturated Bond Bond Activation Zhu, Lizhao Kinjo, Rei Single-nitrogen atom incorporation into B=B bond via the N=N bond splitting of diazo compound and diazirine |
| title | Single-nitrogen atom incorporation into B=B bond via the N=N bond splitting of diazo compound and diazirine |
| title_full | Single-nitrogen atom incorporation into B=B bond via the N=N bond splitting of diazo compound and diazirine |
| title_fullStr | Single-nitrogen atom incorporation into B=B bond via the N=N bond splitting of diazo compound and diazirine |
| title_full_unstemmed | Single-nitrogen atom incorporation into B=B bond via the N=N bond splitting of diazo compound and diazirine |
| title_short | Single-nitrogen atom incorporation into B=B bond via the N=N bond splitting of diazo compound and diazirine |
| title_sort | single nitrogen atom incorporation into b b bond via the n n bond splitting of diazo compound and diazirine |
| topic | Science::Chemistry B-B Unsaturated Bond Bond Activation |
| url | https://hdl.handle.net/10356/171089 |
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