Palladium‐Catalyzed C2−H Arylation of Unprotected (N−H)‐Indoles “On Water” Using Primary Diamantyl Phosphine Oxides as a Class of Primary Phosphine Oxide Ligands
Palladium‐Catalyzed C2−H Arylation of Unprotected (N−H)‐Indoles “On Water” Using Primary Diamantyl Phosphine Oxides as a Class of Primary Phosphine Oxide Ligands
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DOI：
10.1002/cctc.201800187
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发表时间：
2018-07
期刊：
影响因子：
4.5
通讯作者：
Oana Moncea;D. Poinsot;A. Fokin;P. Schreiner;Jean‐Cyrille Hierso
中科院分区：
文献类型：
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作者：
Oana Moncea;D. Poinsot;A. Fokin;P. Schreiner;Jean‐Cyrille Hierso
我们提出了Pd催化的(N−H) -吲哚与功能化卤代芳烃“在水中”的芳基化，使用迄今未测试的伯胺酰膦氧化物（PPO）作为配体。通过使用功能化碘芳烃和N -未保护的吲哚，实现了显著的C2−H基化选择性。我们通过比较与L1结构相关的一组基于diamantane的化合物，证明原位生成的（9 -羟基diamant - 4 - yl）磷化氢L1的氧化物是反应效率的关键。我们的结果证明了新的PPO配体对未保护（N−H）‐杂环的C−H功能化的能力。
We present the Pd‐catalyzed arylation of (N−H)‐indoles with functionalized haloarenes “on water” using hitherto untested primary diamantyl phosphine oxides (PPO) as ligands. Remarkable C2−H arylation selectivity was achieved by employing functionalized iodoarenes and N‐unprotected indoles. We provide evidence that the in situ generated oxide of (9‐hydroxydiamant‐4‐yl)phosphine L1 is key for the reaction efficiency by comparing a set of diamantane‐based compounds structurally related to L1. Our results demonstrate the power of the new PPO ligands for the C−H functionalization of unprotected (N−H)‐heterocycles.