Cu–Bpin-mediated dimerization of 4,4-dichloro-2-butenoic acid derivatives enables the synthesis of densely functionalized cyclopropanes
4,4-Dichloro-2-butenoic acid derivatives are shown to undergo a rare dimerization process when reacted with bis(pinacolato)diboron under copper catalysis. The reaction provides densely functionalized products with excellent levels of chemo-, regio-, and diastereoselectivity. This high degree of func...
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| Format: | Article |
| Language: | English |
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Beilstein-Institut
2025-05-01
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| Series: | Beilstein Journal of Organic Chemistry |
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| Online Access: | https://doi.org/10.3762/bjoc.21.71 |
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| author | Patricia Gómez-Roibás Andrea Chaves-Pouso Martín Fañanás-Mastral |
| author_facet | Patricia Gómez-Roibás Andrea Chaves-Pouso Martín Fañanás-Mastral |
| author_sort | Patricia Gómez-Roibás |
| collection | DOAJ |
| description | 4,4-Dichloro-2-butenoic acid derivatives are shown to undergo a rare dimerization process when reacted with bis(pinacolato)diboron under copper catalysis. The reaction provides densely functionalized products with excellent levels of chemo-, regio-, and diastereoselectivity. This high degree of functionalization makes these products versatile building blocks for the stereoselective synthesis of chlorocyclopropanes. |
| format | Article |
| id | doaj-art-b056cf6a00a14a7f91ae5bf16c4bde64 |
| institution | OA Journals |
| issn | 1860-5397 |
| language | English |
| publishDate | 2025-05-01 |
| publisher | Beilstein-Institut |
| record_format | Article |
| series | Beilstein Journal of Organic Chemistry |
| spelling | doaj-art-b056cf6a00a14a7f91ae5bf16c4bde642025-08-20T02:05:36ZengBeilstein-InstitutBeilstein Journal of Organic Chemistry1860-53972025-05-0121187788310.3762/bjoc.21.711860-5397-21-71Cu–Bpin-mediated dimerization of 4,4-dichloro-2-butenoic acid derivatives enables the synthesis of densely functionalized cyclopropanesPatricia Gómez-Roibás0Andrea Chaves-Pouso1Martín Fañanás-Mastral2Centro Singular de Investigación en Química Biolóxica e Materiais Moleculares (CiQUS), Universidade de Santiago de Compostela, 15782 Santiago de Compostela, Spain Centro Singular de Investigación en Química Biolóxica e Materiais Moleculares (CiQUS), Universidade de Santiago de Compostela, 15782 Santiago de Compostela, Spain Centro Singular de Investigación en Química Biolóxica e Materiais Moleculares (CiQUS), Universidade de Santiago de Compostela, 15782 Santiago de Compostela, Spain 4,4-Dichloro-2-butenoic acid derivatives are shown to undergo a rare dimerization process when reacted with bis(pinacolato)diboron under copper catalysis. The reaction provides densely functionalized products with excellent levels of chemo-, regio-, and diastereoselectivity. This high degree of functionalization makes these products versatile building blocks for the stereoselective synthesis of chlorocyclopropanes.https://doi.org/10.3762/bjoc.21.71chlorocyclopropanescoppercyclization4,4-dichloro-2-butenoic acid derivativesdimerization |
| spellingShingle | Patricia Gómez-Roibás Andrea Chaves-Pouso Martín Fañanás-Mastral Cu–Bpin-mediated dimerization of 4,4-dichloro-2-butenoic acid derivatives enables the synthesis of densely functionalized cyclopropanes Beilstein Journal of Organic Chemistry chlorocyclopropanes copper cyclization 4,4-dichloro-2-butenoic acid derivatives dimerization |
| title | Cu–Bpin-mediated dimerization of 4,4-dichloro-2-butenoic acid derivatives enables the synthesis of densely functionalized cyclopropanes |
| title_full | Cu–Bpin-mediated dimerization of 4,4-dichloro-2-butenoic acid derivatives enables the synthesis of densely functionalized cyclopropanes |
| title_fullStr | Cu–Bpin-mediated dimerization of 4,4-dichloro-2-butenoic acid derivatives enables the synthesis of densely functionalized cyclopropanes |
| title_full_unstemmed | Cu–Bpin-mediated dimerization of 4,4-dichloro-2-butenoic acid derivatives enables the synthesis of densely functionalized cyclopropanes |
| title_short | Cu–Bpin-mediated dimerization of 4,4-dichloro-2-butenoic acid derivatives enables the synthesis of densely functionalized cyclopropanes |
| title_sort | cu bpin mediated dimerization of 4 4 dichloro 2 butenoic acid derivatives enables the synthesis of densely functionalized cyclopropanes |
| topic | chlorocyclopropanes copper cyclization 4,4-dichloro-2-butenoic acid derivatives dimerization |
| url | https://doi.org/10.3762/bjoc.21.71 |
| work_keys_str_mv | AT patriciagomezroibas cubpinmediateddimerizationof44dichloro2butenoicacidderivativesenablesthesynthesisofdenselyfunctionalizedcyclopropanes AT andreachavespouso cubpinmediateddimerizationof44dichloro2butenoicacidderivativesenablesthesynthesisofdenselyfunctionalizedcyclopropanes AT martinfananasmastral cubpinmediateddimerizationof44dichloro2butenoicacidderivativesenablesthesynthesisofdenselyfunctionalizedcyclopropanes |