Iodo(III)-Meyer-Schuster rearrangement of propargylic alcohols promoted by benziodoxole triflate
Benziodoxole triflate (BXT), a cyclic iodine(III) electrophile, has been found to promote a rearrangement of propargylic alcohols into α,β-unsaturated ketones bearing an α-λ3-iodanyl group. This iodo(III)-Meyer-Schuster rearrangement proceeds under mild conditions and tolerates a variety of function...
| Main Authors: | , , |
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| Other Authors: | |
| Format: | Journal Article |
| Language: | English |
| Published: |
2022
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| Online Access: | https://hdl.handle.net/10356/160362 |
| _version_ | 1811689456073179136 |
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| author | Laskar, Roshayed Ali Ding, Wei Yoshikai, Naohiko |
| author2 | School of Physical and Mathematical Sciences |
| author_facet | School of Physical and Mathematical Sciences Laskar, Roshayed Ali Ding, Wei Yoshikai, Naohiko |
| author_sort | Laskar, Roshayed Ali |
| collection | NTU |
| description | Benziodoxole triflate (BXT), a cyclic iodine(III) electrophile, has been found to promote a rearrangement of propargylic alcohols into α,β-unsaturated ketones bearing an α-λ3-iodanyl group. This iodo(III)-Meyer-Schuster rearrangement proceeds under mild conditions and tolerates a variety of functionalized propargylic alcohols, thus complementing previously reported halogen-intercepted Meyer-Schuster rearrangement. The α-λ3-iodanylenones can be utilized for facile Pd-catalyzed cross-coupling for the synthesis of multisubstituted enones. |
| first_indexed | 2024-10-01T05:48:23Z |
| format | Journal Article |
| id | ntu-10356/160362 |
| institution | Nanyang Technological University |
| language | English |
| last_indexed | 2024-10-01T05:48:23Z |
| publishDate | 2022 |
| record_format | dspace |
| spelling | ntu-10356/1603622022-07-20T02:05:53Z Iodo(III)-Meyer-Schuster rearrangement of propargylic alcohols promoted by benziodoxole triflate Laskar, Roshayed Ali Ding, Wei Yoshikai, Naohiko School of Physical and Mathematical Sciences Science::Chemistry Benziodoxole Triflate Unsaturated Ketones Benziodoxole triflate (BXT), a cyclic iodine(III) electrophile, has been found to promote a rearrangement of propargylic alcohols into α,β-unsaturated ketones bearing an α-λ3-iodanyl group. This iodo(III)-Meyer-Schuster rearrangement proceeds under mild conditions and tolerates a variety of functionalized propargylic alcohols, thus complementing previously reported halogen-intercepted Meyer-Schuster rearrangement. The α-λ3-iodanylenones can be utilized for facile Pd-catalyzed cross-coupling for the synthesis of multisubstituted enones. Agency for Science, Technology and Research (A*STAR) Ministry of Education (MOE) This work was supported by the Singapore Ministry of Education Academic Research Funds Tier 2 (MOE2016-T2-2- 043) and Tier 1 (RG114/18) as well as the Agency for Science, Technology and Research (A*STAR) AME IRG grant (A2083c0056). 2022-07-20T02:05:53Z 2022-07-20T02:05:53Z 2021 Journal Article Laskar, R. A., Ding, W. & Yoshikai, N. (2021). Iodo(III)-Meyer-Schuster rearrangement of propargylic alcohols promoted by benziodoxole triflate. Organic Letters, 23(3), 1113-1117. https://dx.doi.org/10.1021/acs.orglett.1c00039 1523-7060 https://hdl.handle.net/10356/160362 10.1021/acs.orglett.1c00039 33439023 2-s2.0-85099924729 3 23 1113 1117 en MOE2016-T2-2-043 RG114/18 A2083c0056 Organic Letters © 2021 American Chemical Society. All rights reserved. |
| spellingShingle | Science::Chemistry Benziodoxole Triflate Unsaturated Ketones Laskar, Roshayed Ali Ding, Wei Yoshikai, Naohiko Iodo(III)-Meyer-Schuster rearrangement of propargylic alcohols promoted by benziodoxole triflate |
| title | Iodo(III)-Meyer-Schuster rearrangement of propargylic alcohols promoted by benziodoxole triflate |
| title_full | Iodo(III)-Meyer-Schuster rearrangement of propargylic alcohols promoted by benziodoxole triflate |
| title_fullStr | Iodo(III)-Meyer-Schuster rearrangement of propargylic alcohols promoted by benziodoxole triflate |
| title_full_unstemmed | Iodo(III)-Meyer-Schuster rearrangement of propargylic alcohols promoted by benziodoxole triflate |
| title_short | Iodo(III)-Meyer-Schuster rearrangement of propargylic alcohols promoted by benziodoxole triflate |
| title_sort | iodo iii meyer schuster rearrangement of propargylic alcohols promoted by benziodoxole triflate |
| topic | Science::Chemistry Benziodoxole Triflate Unsaturated Ketones |
| url | https://hdl.handle.net/10356/160362 |
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