Abstract

Functionally substituted indole derivatives are important intermediates for the synthesis of new potential drug candidates exhibiting strong bioactivities. Over the past few years, significant progress has been made in the direct C–H functionalization of the indole ring through the usage of metal-catalyzed intermolecular cross-coupling with diazo compounds. Directing group strategy provides a unique possibility for selective insertion of carbenes catalytically generated from diazo compounds into challenging indole C2–H and C7–H bonds. This short review summarizes recent advances in carbenoid functionalization of indole derivatives under chelation-controlled metal catalysis.

1 Introduction

2 Indole C2 Alkylation with α-Diazotized Meldrum’s Acid

3 Indole C2 Alkylation with Diazomalonate Derivatives and Related Compounds

4 Indole C7 Alkylation with Diazomalonates and Related Compounds

5 Tandem Indole C2–H Alkylation/Cyclization

6 Indoline C7 Alkylation with Diazomalonates and Related Compounds

7 Tandem Indoline C7–H Alkylation/Cyclization

8 Conclusion

Functionally substituted indole derivatives are important intermediates for the synthesis of new potential drug candidates exhibiting strong bioactivities. Over the past few years, significant progress has been made in the direct C–H functionalization of the indole ring through the usage of metal-catalyzed intermolecular cross-coupling with diazo compounds. Directing group strategy provides a unique possibility for selective insertion of carbenes catalytically generated from diazo compounds into challenging indole C2–H and C7–H bonds. This short review summarizes recent advances in carbenoid functionalization of indole derivatives under chelation-controlled metal catalysis.

1 Introduction

2 Indole C2 Alkylation with α-Diazotized Meldrum’s Acid

3 Indole C2 Alkylation with Diazomalonate Derivatives and Related Compounds

4 Indole C7 Alkylation with Diazomalonates and Related Compounds

5 Tandem Indole C2–H Alkylation/Cyclization

6 Indoline C7 Alkylation with Diazomalonates and Related Compounds

7 Tandem Indoline C7–H Alkylation/Cyclization

8 Conclusion

中文翻译：

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通过螯合辅助金属碳氢化合物CH键的官能团选择性合成2-和7-取代的吲哚衍生物

摘要

功能性取代的吲哚衍生物是用于合成具有强大生物活性的新型潜在候选药物的重要中间体。在过去的几年中，通过使用金属催化的重氮分子间交叉偶联，在吲哚环的直接C–H功能化方面取得了重大进展。指导基团策略为将重氮化合物催化生成的卡宾选择性插入具有挑战性的吲哚C2-H和C7-H键提供了独特的可能性。这篇简短的综述总结了在螯合控制的金属催化下吲哚衍生物类胡萝卜素功能化的最新进展。

1引言

2吲哚C2与α-重氮化的杂色酸的烷基化

3吲哚C2与重氮丙二酸酯衍生物及相关化合物的烷基化

4吲哚C7与重氮丙二酸酯和相关化合物的烷基化

5串联吲哚C2-H烷基化/环化

6重氮丙二酸酯和相关化合物的二氢吲哚C7烷基化

7串联二氢吲哚C7–H烷基化/环化

8结论

功能性取代的吲哚衍生物是用于合成具有强大生物活性的新型潜在候选药物的重要中间体。在过去的几年中，通过使用金属催化的重氮分子间交叉偶联，在吲哚环的直接C–H功能化方面取得了重大进展。指导基团策略为将重氮化合物催化生成的卡宾选择性插入具有挑战性的吲哚C2-H和C7-H键提供了独特的可能性。这篇简短的综述总结了在螯合控制的金属催化下吲哚衍生物类胡萝卜素功能化的最新进展。

1引言

2吲哚C2与α-重氮化的杂色酸的烷基化

3吲哚C2与重氮丙二酸酯衍生物及相关化合物的烷基化

4吲哚C7与重氮丙二酸酯和相关化合物的烷基化

5串联吲哚C2-H烷基化/环化

6重氮丙二酸酯和相关化合物的二氢吲哚C7烷基化

7串联二氢吲哚C7–H烷基化/环化

8结论