Cobalt-catalyzed N-O and C-C bond cleavage in 1,2-oxazetidines : solvent-controlled C-H aminomethylation and hydroxymethylation of heteroarenes
An efficient cobalt-catalyzed ring-opening reaction of bench-stable 1,2-oxazetidines with heteroarenes was unprecedentedly developed. The sustainable Cp *Co(III) catalyst enables a distinctive merger of C-H activation with concomitant N-O and C-C cleavages of 1,2-oxazetidine, leading to site-selecti...
| Main Authors: | , , , , |
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| Other Authors: | |
| Format: | Journal Article |
| Language: | English |
| Published: |
2021
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| Subjects: | |
| Online Access: | https://hdl.handle.net/10356/147449 |
| _version_ | 1826128889291735040 |
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| author | Li, Song Shi, Pengfei Liu, Rui-Hua Hu, Xu-Hong Loh, Teck-Peng |
| author2 | School of Physical and Mathematical Sciences |
| author_facet | School of Physical and Mathematical Sciences Li, Song Shi, Pengfei Liu, Rui-Hua Hu, Xu-Hong Loh, Teck-Peng |
| author_sort | Li, Song |
| collection | NTU |
| description | An efficient cobalt-catalyzed ring-opening reaction of bench-stable 1,2-oxazetidines with heteroarenes was unprecedentedly developed. The sustainable Cp *Co(III) catalyst enables a distinctive merger of C-H activation with concomitant N-O and C-C cleavages of 1,2-oxazetidine, leading to site-selective C-H aminomethylation and hydroxymethylation of heteroaromatic compounds containing a broad range of functional groups. Preliminary control experiments unravel some essential mechanistic features of this one-pot transformation. |
| first_indexed | 2024-10-01T07:32:15Z |
| format | Journal Article |
| id | ntu-10356/147449 |
| institution | Nanyang Technological University |
| language | English |
| last_indexed | 2024-10-01T07:32:15Z |
| publishDate | 2021 |
| record_format | dspace |
| spelling | ntu-10356/1474492021-04-01T08:57:20Z Cobalt-catalyzed N-O and C-C bond cleavage in 1,2-oxazetidines : solvent-controlled C-H aminomethylation and hydroxymethylation of heteroarenes Li, Song Shi, Pengfei Liu, Rui-Hua Hu, Xu-Hong Loh, Teck-Peng School of Physical and Mathematical Sciences Science::Chemistry Derivatives Synthesis Aryl Halides An efficient cobalt-catalyzed ring-opening reaction of bench-stable 1,2-oxazetidines with heteroarenes was unprecedentedly developed. The sustainable Cp *Co(III) catalyst enables a distinctive merger of C-H activation with concomitant N-O and C-C cleavages of 1,2-oxazetidine, leading to site-selective C-H aminomethylation and hydroxymethylation of heteroaromatic compounds containing a broad range of functional groups. Preliminary control experiments unravel some essential mechanistic features of this one-pot transformation. Financial support from the NNSFC (21702106), the Natural Science Foundation of Jiangsu Province (BK20170967), and the Start-up Grant from Nanjing Tech University (39839101 and 39837101) is gratefully acknowledged. We also acknowledge the SICAM Fellowship from the Jiangsu National Synergetic Innovation Center for Advanced Materials. 2021-04-01T08:57:20Z 2021-04-01T08:57:20Z 2019 Journal Article Li, S., Shi, P., Liu, R., Hu, X. & Loh, T. (2019). Cobalt-catalyzed N-O and C-C bond cleavage in 1,2-oxazetidines : solvent-controlled C-H aminomethylation and hydroxymethylation of heteroarenes. Organic Letters, 21(6), 1602-1606. https://dx.doi.org/10.1021/acs.orglett.9b00141 1523-7060 https://hdl.handle.net/10356/147449 10.1021/acs.orglett.9b00141 30807182 2-s2.0-85062958514 6 21 1602 1606 en Organic Letters © 2019 American Chemical Society. All rights reserved. |
| spellingShingle | Science::Chemistry Derivatives Synthesis Aryl Halides Li, Song Shi, Pengfei Liu, Rui-Hua Hu, Xu-Hong Loh, Teck-Peng Cobalt-catalyzed N-O and C-C bond cleavage in 1,2-oxazetidines : solvent-controlled C-H aminomethylation and hydroxymethylation of heteroarenes |
| title | Cobalt-catalyzed N-O and C-C bond cleavage in 1,2-oxazetidines : solvent-controlled C-H aminomethylation and hydroxymethylation of heteroarenes |
| title_full | Cobalt-catalyzed N-O and C-C bond cleavage in 1,2-oxazetidines : solvent-controlled C-H aminomethylation and hydroxymethylation of heteroarenes |
| title_fullStr | Cobalt-catalyzed N-O and C-C bond cleavage in 1,2-oxazetidines : solvent-controlled C-H aminomethylation and hydroxymethylation of heteroarenes |
| title_full_unstemmed | Cobalt-catalyzed N-O and C-C bond cleavage in 1,2-oxazetidines : solvent-controlled C-H aminomethylation and hydroxymethylation of heteroarenes |
| title_short | Cobalt-catalyzed N-O and C-C bond cleavage in 1,2-oxazetidines : solvent-controlled C-H aminomethylation and hydroxymethylation of heteroarenes |
| title_sort | cobalt catalyzed n o and c c bond cleavage in 1 2 oxazetidines solvent controlled c h aminomethylation and hydroxymethylation of heteroarenes |
| topic | Science::Chemistry Derivatives Synthesis Aryl Halides |
| url | https://hdl.handle.net/10356/147449 |
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