Bismuth-Catalyzed Oxidative Coupling of Arylboronic Acids with Triflate and Nonaflate Salts,Journal of the American Chemical Society

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Bismuth-Catalyzed Oxidative Coupling of Arylboronic Acids with Triflate and Nonaflate Salts
Journal of the American Chemical Society ( IF 14.4 ) Pub Date : 2020-06-14 , DOI: 10.1021/jacs.0c05343
Oriol Planas ₁ , Vytautas Peciukenas ₁ , Josep Cornella ₁

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Herein we present a Bi-catalyzed cross-coupling of arylboronic acids with perfluoroalkyl sulfonate salts based on a Bi(III)/Bi(V) redox cycle. An electron-deficient sulfone ligand proved to be key for the successful implementation of this protocol, which allows the unusual construction of C(sp2)–O bonds using commercially available NaOTf and KONf as coupling partners. Preliminary mechanistic studies as well as theoretical investigations reveal the intermediacy of a highly electrophilic Bi(V) species, which rapidly eliminates phenyl triflate.

中文翻译：

芳基硼酸与三氟甲磺酸盐和九氟甲磺酸盐的铋催化氧化偶联

在此，我们提出了基于 Bi(III)/Bi(V) 氧化还原循环的芳基硼酸与全氟烷基磺酸盐的 Bi 催化交叉偶联。缺电子的砜配体被证明是成功实施该协议的关键，它允许使用市售的 NaOTf 和 KONf 作为偶联伙伴构建 C(sp2)-O 键。初步的机理研究和理论研究揭示了高度亲电子的 Bi(V) 物种的中间体，它可以快速消除三氟甲磺酸苯酯。

更新日期：2020-06-14

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