Iodine(III)-mediated halogenations of acyclic monoterpenoids
Five different halofunctionalizations of acyclic monoterpenoids were performed using a combination of a hypervalent iodine(III) reagent and a halide salt. In this manner, the dibromination, the bromo(trifluoro)acetoxylation, the bromohydroxylation, the iodo(trifluoro)acetoxylation or the ene-type ch...
| Main Authors: | , , , , |
|---|---|
| Format: | Article |
| Language: | English |
| Published: |
Beilstein-Institut
2018-05-01
|
| Series: | Beilstein Journal of Organic Chemistry |
| Subjects: | |
| Online Access: | https://doi.org/10.3762/bjoc.14.96 |
| _version_ | 1819175167339790336 |
|---|---|
| author | Laure Peilleron Tatyana D. Grayfer Joëlle Dubois Robert H. Dodd Kevin Cariou |
| author_facet | Laure Peilleron Tatyana D. Grayfer Joëlle Dubois Robert H. Dodd Kevin Cariou |
| author_sort | Laure Peilleron |
| collection | DOAJ |
| description | Five different halofunctionalizations of acyclic monoterpenoids were performed using a combination of a hypervalent iodine(III) reagent and a halide salt. In this manner, the dibromination, the bromo(trifluoro)acetoxylation, the bromohydroxylation, the iodo(trifluoro)acetoxylation or the ene-type chlorination of the distal trisubstituted double bond occurred with excellent selectivity and moderate to good yields. |
| first_indexed | 2024-12-22T20:50:34Z |
| format | Article |
| id | doaj.art-c3d87339091a4ae8ac16860f2df045e5 |
| institution | Directory Open Access Journal |
| issn | 1860-5397 |
| language | English |
| last_indexed | 2024-12-22T20:50:34Z |
| publishDate | 2018-05-01 |
| publisher | Beilstein-Institut |
| record_format | Article |
| series | Beilstein Journal of Organic Chemistry |
| spelling | doaj.art-c3d87339091a4ae8ac16860f2df045e52022-12-21T18:13:06ZengBeilstein-InstitutBeilstein Journal of Organic Chemistry1860-53972018-05-011411103111110.3762/bjoc.14.961860-5397-14-96Iodine(III)-mediated halogenations of acyclic monoterpenoidsLaure Peilleron0Tatyana D. Grayfer1Joëlle Dubois2Robert H. Dodd3Kevin Cariou4Institut de Chimie des Substances Naturelles, CNRS UPR 2301, Université Paris-Sud, Université Paris-Saclay, Avenue de la Terrasse, 91198 Gif-sur-Yvette, FranceInstitut de Chimie des Substances Naturelles, CNRS UPR 2301, Université Paris-Sud, Université Paris-Saclay, Avenue de la Terrasse, 91198 Gif-sur-Yvette, FranceInstitut de Chimie des Substances Naturelles, CNRS UPR 2301, Université Paris-Sud, Université Paris-Saclay, Avenue de la Terrasse, 91198 Gif-sur-Yvette, FranceInstitut de Chimie des Substances Naturelles, CNRS UPR 2301, Université Paris-Sud, Université Paris-Saclay, Avenue de la Terrasse, 91198 Gif-sur-Yvette, FranceInstitut de Chimie des Substances Naturelles, CNRS UPR 2301, Université Paris-Sud, Université Paris-Saclay, Avenue de la Terrasse, 91198 Gif-sur-Yvette, FranceFive different halofunctionalizations of acyclic monoterpenoids were performed using a combination of a hypervalent iodine(III) reagent and a halide salt. In this manner, the dibromination, the bromo(trifluoro)acetoxylation, the bromohydroxylation, the iodo(trifluoro)acetoxylation or the ene-type chlorination of the distal trisubstituted double bond occurred with excellent selectivity and moderate to good yields.https://doi.org/10.3762/bjoc.14.96halogenationhypervalent iodinemonoterpenes |
| spellingShingle | Laure Peilleron Tatyana D. Grayfer Joëlle Dubois Robert H. Dodd Kevin Cariou Iodine(III)-mediated halogenations of acyclic monoterpenoids Beilstein Journal of Organic Chemistry halogenation hypervalent iodine monoterpenes |
| title | Iodine(III)-mediated halogenations of acyclic monoterpenoids |
| title_full | Iodine(III)-mediated halogenations of acyclic monoterpenoids |
| title_fullStr | Iodine(III)-mediated halogenations of acyclic monoterpenoids |
| title_full_unstemmed | Iodine(III)-mediated halogenations of acyclic monoterpenoids |
| title_short | Iodine(III)-mediated halogenations of acyclic monoterpenoids |
| title_sort | iodine iii mediated halogenations of acyclic monoterpenoids |
| topic | halogenation hypervalent iodine monoterpenes |
| url | https://doi.org/10.3762/bjoc.14.96 |
| work_keys_str_mv | AT laurepeilleron iodineiiimediatedhalogenationsofacyclicmonoterpenoids AT tatyanadgrayfer iodineiiimediatedhalogenationsofacyclicmonoterpenoids AT joelledubois iodineiiimediatedhalogenationsofacyclicmonoterpenoids AT roberthdodd iodineiiimediatedhalogenationsofacyclicmonoterpenoids AT kevincariou iodineiiimediatedhalogenationsofacyclicmonoterpenoids |