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Base-Activated Latent Heteroaromatic Sulfinates as Nucleophilic Coupling Partners in Palladium-Catalyzed Cross-Coupling Reactions.

ABSTRACT: 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.

SUBMITTER: Cook XAF

PROVIDER: S-EPMC8518705 | biostudies-literature | 2021 Oct

REPOSITORIES: biostudies-literature

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Base-Activated Latent Heteroaromatic Sulfinates as Nucleophilic Coupling Partners in Palladium-Catalyzed Cross-Coupling Reactions.

Cook Xinlan A F XAF Pantaine Loïc R E LRE Blakemore David C DC Moses Ian B IB Sach Neal W NW Shavnya Andre A Willis Michael C MC

Angewandte Chemie (International ed. in English) 20210908 41

Heteroaromatic sulfinates are effective nucleophilic reagents in Pd<sup>0</sup> -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 ...[more]

PMID: 34342107

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