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Borane-catalyzed stereoselective C–H Insertion, cyclopropanation, and ring-opening reactions
Citation
Dasgupta, A and Babaahmadi, R and Slater, B and Yates, BF and Ariafard, A and Melen, RL, Borane-catalyzed stereoselective C-H Insertion, cyclopropanation, and ring-opening reactions, Chem, 6, (9) pp. 2364-2381. ISSN 2451-9308 (2020) [Refereed Article]
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DOI: doi:10.1016/j.chempr.2020.06.035
Abstract
Lewis acidic boranes have been shown to be effective metal-free catalysts for highly selective reactions of donor-acceptor diazo compounds to a range of substrates. The reactions of α-aryl α-diazoesters with nitrogen heterocycles indole or pyrrole selectively generate C3 and C2 C–H insertion products, respectively, in good to excellent yields even when using unprotected indoles. Alternatively, benzofuran, indene, and alkene substrates give exclusively cyclopropanated products with α-aryl α-diazoesters, whereas the reactions with furans lead to ring-opening. Comprehensive theoretical calculations have been used to explain the differing reactivities and high selectivities of these reactions. Overall, this work demonstrates the selective metal-free catalytic reactions of α-aryl α-diazoesters with (hetero)cycles and alkenes. This simple, mild reaction protocol represents an alternative to the commonly used precious metal systems and may provide future applications in the generation of biologically active compounds.
Item Details
| Item Type: | Refereed Article |
|---|---|
| Keywords: | DFT analysis, cyclopropanation, C–H activation, borane catalysis, ring- opening reactions |
| Research Division: | Chemical Sciences |
| Research Group: | Organic chemistry |
| Research Field: | Physical organic chemistry |
| Objective Division: | Expanding Knowledge |
| Objective Group: | Expanding knowledge |
| Objective Field: | Expanding knowledge in the chemical sciences |
| UTAS Author: | Babaahmadi, R (Mr Rasool Babaahmadi) |
| UTAS Author: | Yates, BF (Professor Brian Yates) |
| UTAS Author: | Ariafard, A (Associate Professor Alireza Ariafard) |
| ID Code: | 142015 |
| Year Published: | 2020 |
| Funding Support: | Australian Research Council (DP180100904) |
| Web of Science® Times Cited: | 6 |
| Deposited By: | Chemistry |
| Deposited On: | 2020-12-08 |
| Last Modified: | 2021-01-27 |
| Downloads: | 0 |
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