Base-Activated Latent Heteroaromatic Sulfinates as Nucleophilic Coupling Partners in Palladium-Catalyzed Cross-Coupling Reactions,Angewandte Chemie International Edition

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Base-Activated Latent Heteroaromatic Sulfinates as Nucleophilic Coupling Partners in Palladium-Catalyzed Cross-Coupling Reactions
Angewandte Chemie International Edition ( IF 16.1 ) Pub Date : 2021-08-02 , DOI: 10.1002/anie.202109146
Xinlan A F Cook ₁ , Loïc R E Pantaine ₁ , David C Blakemore ₂ , Ian B Moses ₃ , Neal W Sach ₄ , Andre Shavnya ₂ , Michael C Willis ₁

Affiliation

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.

中文翻译：

碱激活的潜在杂芳族亚磺酸盐作为钯催化交叉偶联反应中的亲核偶联伙伴

杂芳族亚磺酸盐是Pd ⁰催化的与芳基卤化物交叉偶联反应中有效的亲核试剂。然而，金属亚磺酸盐的纯化、在反应介质中的溶解可能具有挑战性，并且不耐受多步转化。在这里，我们介绍碱激活的潜在亚磺酸盐试剂：β-腈和β-酯砜。我们表明，在交叉偶联条件下，这些物质原位生成亚磺酸盐，然后与（杂）芳基溴进行有效的钯催化脱亚磺交叉偶联，产生多种联芳基化合物。通过多步底物精制，这些潜在的亚磺酸盐试剂已被证明是稳定的，并且适合放大生产。

更新日期：2021-09-27

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