Nickel(II)-catalyzed addition of aryl and heteroaryl boroxines to the sulfinylamine reagent TrNSO: the catalytic synthesis of sul-finamides, sulfonimidamides and primary sulfonamides
We report a redox-neutral Ni(II)-catalyzed addition of (hetero)aryl boroxines to N-sulfinyltritylamine (TrNSO). The reactions use a catalyst generated from the combination of commercial, air-stable NiCl2·(glyme) and a commercially available bipyridine ligand, and deliver sulfinamide products. The sc...
| Huvudupphovsmän: | , |
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| Materialtyp: | Journal article |
| Språk: | English |
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American Chemical Society
2021
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| _version_ | 1826308430662467584 |
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| author | Lo, PKT Willis, MC |
| author_facet | Lo, PKT Willis, MC |
| author_sort | Lo, PKT |
| collection | OXFORD |
| description | We report a redox-neutral Ni(II)-catalyzed addition of (hetero)aryl boroxines to N-sulfinyltritylamine (TrNSO). The reactions use a catalyst generated from the combination of commercial, air-stable NiCl2·(glyme) and a commercially available bipyridine ligand, and deliver sulfinamide products. The scope of the reaction is established using a sulfonimidamide synthesis, in which the initially formed sulfinamides undergo oxidative chlorination with the inexpensive and safe chlorinating agent, trichloroisocyanuric acid (TCCA), to produce sulfonimidoyl chlorides as key intermediates. These are combined in situ with a range of amines to deliver sulfonimidamides. The sulfonimidoyl chlorides can also be elaborated into primary sulfonamides via hydrolysis, and sulfonimidoyl fluorides via treatment with fluoride. These transformations are all achieved using one-pot procedures. Unprotected, primary sulfinamides are also available. For larger-scale reactions, the catalyst loading can be reduced to 1 mol %. |
| first_indexed | 2024-03-07T07:19:22Z |
| format | Journal article |
| id | oxford-uuid:21f2d0c5-705a-464e-aebf-9d7b4e595602 |
| institution | University of Oxford |
| language | English |
| last_indexed | 2024-03-07T07:19:22Z |
| publishDate | 2021 |
| publisher | American Chemical Society |
| record_format | dspace |
| spelling | oxford-uuid:21f2d0c5-705a-464e-aebf-9d7b4e5956022022-09-20T12:51:13ZNickel(II)-catalyzed addition of aryl and heteroaryl boroxines to the sulfinylamine reagent TrNSO: the catalytic synthesis of sul-finamides, sulfonimidamides and primary sulfonamidesJournal articlehttp://purl.org/coar/resource_type/c_dcae04bcuuid:21f2d0c5-705a-464e-aebf-9d7b4e595602EnglishSymplectic ElementsAmerican Chemical Society2021Lo, PKTWillis, MCWe report a redox-neutral Ni(II)-catalyzed addition of (hetero)aryl boroxines to N-sulfinyltritylamine (TrNSO). The reactions use a catalyst generated from the combination of commercial, air-stable NiCl2·(glyme) and a commercially available bipyridine ligand, and deliver sulfinamide products. The scope of the reaction is established using a sulfonimidamide synthesis, in which the initially formed sulfinamides undergo oxidative chlorination with the inexpensive and safe chlorinating agent, trichloroisocyanuric acid (TCCA), to produce sulfonimidoyl chlorides as key intermediates. These are combined in situ with a range of amines to deliver sulfonimidamides. The sulfonimidoyl chlorides can also be elaborated into primary sulfonamides via hydrolysis, and sulfonimidoyl fluorides via treatment with fluoride. These transformations are all achieved using one-pot procedures. Unprotected, primary sulfinamides are also available. For larger-scale reactions, the catalyst loading can be reduced to 1 mol %. |
| spellingShingle | Lo, PKT Willis, MC Nickel(II)-catalyzed addition of aryl and heteroaryl boroxines to the sulfinylamine reagent TrNSO: the catalytic synthesis of sul-finamides, sulfonimidamides and primary sulfonamides |
| title | Nickel(II)-catalyzed addition of aryl and heteroaryl boroxines to the sulfinylamine reagent TrNSO: the catalytic synthesis of sul-finamides, sulfonimidamides and primary sulfonamides |
| title_full | Nickel(II)-catalyzed addition of aryl and heteroaryl boroxines to the sulfinylamine reagent TrNSO: the catalytic synthesis of sul-finamides, sulfonimidamides and primary sulfonamides |
| title_fullStr | Nickel(II)-catalyzed addition of aryl and heteroaryl boroxines to the sulfinylamine reagent TrNSO: the catalytic synthesis of sul-finamides, sulfonimidamides and primary sulfonamides |
| title_full_unstemmed | Nickel(II)-catalyzed addition of aryl and heteroaryl boroxines to the sulfinylamine reagent TrNSO: the catalytic synthesis of sul-finamides, sulfonimidamides and primary sulfonamides |
| title_short | Nickel(II)-catalyzed addition of aryl and heteroaryl boroxines to the sulfinylamine reagent TrNSO: the catalytic synthesis of sul-finamides, sulfonimidamides and primary sulfonamides |
| title_sort | nickel ii catalyzed addition of aryl and heteroaryl boroxines to the sulfinylamine reagent trnso the catalytic synthesis of sul finamides sulfonimidamides and primary sulfonamides |
| work_keys_str_mv | AT lopkt nickeliicatalyzedadditionofarylandheteroarylboroxinestothesulfinylaminereagenttrnsothecatalyticsynthesisofsulfinamidessulfonimidamidesandprimarysulfonamides AT willismc nickeliicatalyzedadditionofarylandheteroarylboroxinestothesulfinylaminereagenttrnsothecatalyticsynthesisofsulfinamidessulfonimidamidesandprimarysulfonamides |