Ylide-Functionalized Diisopropyl Phosphine (prYPhos): A Ligand for Selective Suzuki-Miyaura Couplings of Aryl Chlorides,Advanced Synthesis & Catalysis

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Ylide-Functionalized Diisopropyl Phosphine (prYPhos): A Ligand for Selective Suzuki-Miyaura Couplings of Aryl Chlorides
Advanced Synthesis & Catalysis ( IF 4.4 ) Pub Date : 2022-05-25 , DOI: 10.1002/adsc.202200321
Xiao-Jing Wei ₁ , Bingxiang Xue ₁ , Jens Handelmann ₁ , Zhiyong Hu ₁ , Heidar Darmandeh ₁ , Viktoria Däschlein-Gessner ₂ , Lukas J. Goossen ₁

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The ylide-functionalized diisopropyl phosphine (prYPhos) promotes Pd-catalyzed Suzuki-Miyaura couplings of aryl chlorides and bromides with arylboronic acids. Using Pd₂(dba)₃/prYPhos as the catalyst and K₂CO₃ as the base, various (hetero)biaryls were synthesized in 45–98% yields at mild reaction conditions, tolerating sensitive functional groups and steric hindrance. The electron rich, sterically demanding ligand induces a high selectivity for halides versus triflate. Chloroaryl triflates were selectively coupled at the chloride, leaving inherently more reactive triflate groups in place.

中文翻译：

叶立德官能化二异丙基膦 (prYPhos)：芳基氯化物选择性 Suzuki-Miyaura 偶联的配体

叶立德官能化的二异丙基膦 (prYPhos) 可促进 Pd 催化的芳基氯化物和溴化物与芳基硼酸的 Suzuki-Miyaura 偶联。使用 Pd ₂ (dba) ₃ /prYPhos 作为催化剂和 K ₂ CO ₃作为碱，在温和的反应条件下以 45-98% 的收率合成了各种（杂）联芳基化合物，耐受敏感的官能团和空间位阻。富电子、空间要求高的配体对卤化物和三氟甲磺酸盐具有较高的选择性。氯芳基三氟甲磺酸酯在氯化物处选择性偶联，留下固有的更具反应性的三氟甲磺酸酯基团。

更新日期：2022-05-25

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