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：

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碱活化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

在 Pd ⁰催化的与芳基卤化物的交叉偶联反应中，杂芳族亚磺酸盐是有效的亲核试剂。然而，金属亚磺酸盐难以纯化，难以溶解在反应介质中，并且不能耐受多步转化。在这里，我们介绍了碱活化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，这些物种原位生成亚磺酸盐，然后与（杂）芳基溴化物进行有效的钯催化脱亚磺酸交叉偶联，以提供广泛的联芳基化合物。这些潜在的亚磺酸盐试剂已通过多步底物加工证明是稳定的，并且可以放大。