Asymmetric Borylation of Remote C(sp3)-H Bonds for the Construction of Compounds with Three-Dimensional Structural Diversity
| Project/Area Number |
20K15269
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| Research Category |
Grant-in-Aid for Early-Career Scientists
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| Allocation Type | Multi-year Fund |
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| Review Section |
Basic Section 33020:Synthetic organic chemistry-related
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| Research Institution | Hokkaido University |
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Principal Investigator |
REYES RONALD・LAZO 北海道大学, 化学反応創成研究拠点, 特任助教 (30845475)
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| Project Period (FY) |
2020-04-01 – 2023-03-31
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| Project Status |
Discontinued (Fiscal Year 2022)
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| Budget Amount *help |
¥4,160,000 (Direct Cost: ¥3,200,000、Indirect Cost: ¥960,000)
Fiscal Year 2023: ¥650,000 (Direct Cost: ¥500,000、Indirect Cost: ¥150,000)
Fiscal Year 2022: ¥780,000 (Direct Cost: ¥600,000、Indirect Cost: ¥180,000)
Fiscal Year 2021: ¥1,040,000 (Direct Cost: ¥800,000、Indirect Cost: ¥240,000)
Fiscal Year 2020: ¥1,690,000 (Direct Cost: ¥1,300,000、Indirect Cost: ¥390,000)
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| Keywords | borylation / asymmetric synthesis / organometallic catalysis / organic synthesis / C-H activation / C-H functionalization / remote C-H bonds / noncovalent interactions |
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| Outline of Research at the Start |
In this work, combined theoretical calculations (AFIR, DFT, etc.) and experimental methodologies will be utilized for the construction of efficient catalytic system that will enable the competent functionalization of remote C-H bonds from simple and readily available feedstocks.
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| Outline of Annual Research Achievements |
With our interest in the development of novel methodologies for the transformation of C-H bonds in readily available feedstock chemicals, we previously demonstrated the competent activation and subsequent asymmetric borylation of g-C(sp3)-H bonds under Ir catalysis. Our collaboration with ICReDD scientists has given us infinite opportunity to further extend the reactivity of our catalytic system. Thus, guided by calculation derived transition-state models, we recently succeeded in the asymmetric borylation of more distal C-H bonds in the aliphatic hydrocarbon chain of common and readily available chemical feedstocks including biomass resources allowing for a more sustainable and efficient organic synthesis. Thereby, the borylation of e-C-H bonds, located five carbons away from the carbonyl group of the substrate, has been achieved - a direct functionalization realized using a modularly designed supramolecular catalytic assembly.
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Report
(3 results)
Research Products
(14 results)
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[Journal Article] Asymmetric Remote C-H Borylation of Aliphatic Amides and Esters with a Modular Iridium Catalyst2020
Author(s)
Reyes, R. L., Sato, M. Iwai, T., Suzuki, K., Maeda, S., and Sawamura, M.
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Journal Title
Science
Volume: 369
Issue: 6506
Pages: 970-974
DOI
Related Report
Peer Reviewed / Int'l Joint Research
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[Presentation] Asymmetric Remote C-H Bond Borylation with a Modular Iridium Catalyst2021
Author(s)
Reyes, R. L., Sato, M., Iwai, T., Suzuki, K., Maeda, S., and Sawamura, M.
Organizer
101st Chemistry Society of Japan (CSJ) Annual Meeting
Related Report
Int'l Joint Research
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[Presentation] Catalytic Enantioselective Remote C-H Borylation of Aliphatic Carboxylic Amides and Esters2021
Author(s)
Reyes, R. L., Sato, M., Masuda, Y., Higashida, K., Iwai, T., Suzuki, K., Maeda, S., and Sawamura, M.
Organizer
67th Organometallic Chemistry Symposium
Related Report
Int'l Joint Research
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[Presentation] Synthesis of Biologically-Relevant Organoboron Compounds through Asymmetric C-H Borylation2021
Author(s)
Reyes, R. L., Sato, M., Chong, S.-G, Higashida, K., Iwai, T., Suzuki, K., Maeda, S., and Sawamura, M.
Organizer
13th International Medicinal Chemistry Symposium
Related Report
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[Presentation] Strategic Construction of Molecular Complexity via Asymmetric Remote C-H Borylation: Building Structural Diversity from Common Feedstock Chemicals2020
Author(s)
Reyes, R. L., Sato, Miyu, Iwai, T., Suzuki, K., Maeda, S., and Sawamura, M
Organizer
Joint Symposium of School of Science and WPI-ICReDD, Hokkaido University
Related Report
Invited
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