Published as part of the Special Section dedicated to Scott E. Denmark on the occasion of his 65^th birthday

Abstract

The Pd-catalyzed 3-arylation of 2-oxindoles with aryl bromides, chlorides and triflates is found to proceed using i-Pr-BI-DIME and Me₂-BI-DIME ligands. The mono-arylation of 3-unsubstituted oxindoles is accomplished using a Pd₂(dba)₃/i-Pr-BI-DIME catalyst system, and gives good yields of 3-aryloxindoles from aryl bromides and chlorides. The arylation of 3-substituted oxindoles is also possible using this catalyst/ligand system. The asymmetric arylation of 3-substituted oxindoles is accomplished using Me₂-BI-DIME to furnish oxindoles bearing a quaternary C-3 stereocenter in enantiomeric ratios of up to 93:7.

The Pd-catalyzed 3-arylation of 2-oxindoles with aryl bromides, chlorides and triflates is found to proceed using i-Pr-BI-DIME and Me₂-BI-DIME ligands. The mono-arylation of 3-unsubstituted oxindoles is accomplished using a Pd₂(dba)₃/i-Pr-BI-DIME catalyst system, and gives good yields of 3-aryloxindoles from aryl bromides and chlorides. The arylation of 3-substituted oxindoles is also possible using this catalyst/ligand system. The asymmetric arylation of 3-substituted oxindoles is accomplished using Me₂-BI-DIME to furnish oxindoles bearing a quaternary C-3 stereocenter in enantiomeric ratios of up to 93:7.

中文翻译：

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使用修饰的BI-DIME配体对羟基吲哚进行对映选择性化

发布时间作为的一部分奉献给斯科特E.丹麦在他65之际特科^次生日

抽象的

发现使用i -Pr-BI-DIME和Me ₂ -BI-DIME配体进行2-氧吲哚与芳基溴化物，氯化物和三氟甲磺酸酯的Pd催化的3-芳基化。使用Pd ₂（dba）₃ / i -Pr-BI-DIME催化剂体系可完成3-未取代的羟吲哚的单芳基化反应，并从芳基溴化物和氯化物获得3-芳基羟吲哚的良好收率。使用该催化剂/配体体系也可以使3-取代的羟吲哚芳基化。使用Me ₂ -BI-DIME提供对映体比率高达93：7的带有季C-3立体中心的羟吲哚，可以完成3-取代的羟吲哚的不对称芳基化反应。

发现使用i -Pr-BI-DIME和Me ₂ -BI-DIME配体进行2-氧吲哚与芳基溴化物，氯化物和三氟甲磺酸酯的Pd催化的3-芳基化。使用Pd ₂（dba）₃ / i -Pr-BI-DIME催化剂体系可完成3-未取代的羟吲哚的单芳基化反应，并从芳基溴化物和氯化物获得3-芳基羟吲哚的良好收率。使用该催化剂/配体体系也可以使3-取代的羟吲哚芳基化。使用Me ₂ -BI-DIME提供对映体比率高达93：7的带有季C-3立体中心的羟吲哚，可以完成3-取代的羟吲哚的不对称芳基化反应。