Base‐Activated Latent Heteroaromatic Sulfinates as Nucleophilic Coupling Partners in Palladium‐Catalyzed Cross‐Coupling Reactions
| Autor: | Ian B. Moses, Neal W. Sach, Loïc R E Pantaine, Andre Shavnya, David C. Blakemore, Xinlan A F Cook, Michael C. Willis |
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| Jazyk: | angličtina |
| Rok vydání: | 2021 |
| Předmět: |
pyridine
chemistry.chemical_element Cross‐Coupling | Hot Paper 010402 general chemistry 01 natural sciences Catalysis Coupling reaction Sulfone chemistry.chemical_compound Nucleophile Pyridine cross-coupling desulfination Research Articles 010405 organic chemistry Aryl sulfone General Chemistry General Medicine palladium Combinatorial chemistry 0104 chemical sciences chemistry Reagent Palladium Research Article |
| Zdroj: | Angewandte Chemie (International Ed. in English) |
| ISSN: | 1521-3773 1433-7851 |
| Popis: | Heteroaromatic sulfinates are effective nucleophilic reagents in Pd0‐catalyzed cross‐coupling reactions with aryl halides. However, metal sulfinate salts can be challenging to purify, solubilize in reaction media, and are not tolerant to multi‐step transformations. Here we introduce base‐activated, latent sulfinate reagents: β‐nitrile and β‐ester sulfones. We show that under the cross‐coupling conditions, these species generate the sulfinate salt in situ, which then undergo efficient palladium‐catalyzed desulfinative cross‐coupling with (hetero)aryl bromides to deliver a broad range of biaryls. These latent sulfinate reagents have proven to be stable through multi‐step substrate elaboration, and amenable to scale‐up. Next‐generation, base‐activated latent sulfinate reagents have been successfully developed for use in the construction of heteroaromatic frameworks, such as 2‐arylpyridines. Under Pd‐catalyzed conditions, these species unmask to give the sulfinate in situ, which then undergoes efficient desulfinative cross‐coupling with an array of (hetero)aryl halides. |
| Databáze: | OpenAIRE |
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