Transition Metal-Catalysed, Direct and Site-Selective N1-, C2- or C3-Arylation of the Indole Nucleus: 20 Years of Improvements

The direct and site‐selective transition metal‐catalysed N1‐, C2‐ or C3‐arylations of indoles have been the subject of almost continuous improvements since their discovery in early 1980s. This research area is mainly motivated by the biological relevance of this class of compounds in order to propos...

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Published in	Advanced synthesis & catalysis Vol. 351; no. 5; pp. 673 - 714
Main Authors	Joucla, Lionel, Djakovitch, Laurent
Format	Journal Article
Language	English
Published	Weinheim WILEY-VCH Verlag 01.03.2009 WILEY‐VCH Verlag Wiley-VCH Verlag
Subjects	arylindoles Buchwald-Hartwig amination Catalysis Chemical Sciences CH activation oxidative coupling site-selective arylation
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Abstract	The direct and site‐selective transition metal‐catalysed N1‐, C2‐ or C3‐arylations of indoles have been the subject of almost continuous improvements since their discovery in early 1980s. This research area is mainly motivated by the biological relevance of this class of compounds in order to propose catalytic alternative syntheses to the well known methodologies involving the formation of the indole ring like the Fischer, Larock, Cacchi, Lautens etc. reactions. Since the late 1990s it has experienced new impulses related to the intensive development of catalytic CH activation. Today, through the intensive studies of Buchwald and Hartwig, the N1‐arylation of indoles has reached sufficient maturity for both academic and industrial applications. On the other hand, the selective C2‐ or C3‐arylation of indoles, initiated by Ohta in the middle 1980s, has become a hot research area these last years following the reports of Sames. Surprisingly, only few reports concern the use of heterogeneous catalysts; however, the application of these emerging methodologies seems to be related to the discovery of industrially attractive systems.
AbstractList	magnified image The direct and site‐selective transition metal‐catalysed N1‐, C2‐ or C3‐arylations of indoles have been the subject of almost continuous improvements since their discovery in early 1980s. This research area is mainly motivated by the biological relevance of this class of compounds in order to propose catalytic alternative syntheses to the well known methodologies involving the formation of the indole ring like the Fischer, Larock, Cacchi, Lautens etc. reactions. Since the late 1990s it has experienced new impulses related to the intensive development of catalytic CH activation. Today, through the intensive studies of Buchwald and Hartwig, the N1‐arylation of indoles has reached sufficient maturity for both academic and industrial applications. On the other hand, the selective C2‐ or C3‐arylation of indoles, initiated by Ohta in the middle 1980s, has become a hot research area these last years following the reports of Sames. Surprisingly, only few reports concern the use of heterogeneous catalysts; however, the application of these emerging methodologies seems to be related to the discovery of industrially attractive systems. The direct and site-selective transition metal-catalysed N1-, C2- or C3-arylations of indoles have been the subject of almost continuous improvements since their discovery in early 1980s. This research area is mainly motivated by the biological relevance of this class of compounds in order to propose catalytic alternative syntheses to the well known methodologies involving the formation of the indole ring like the Fischer, Larock, Cacchi, Lautens etc. reactions. Since the late 1990s it has experienced new impulses related to the intensive development of catalytic CH activation. Today, through the intensive studies of Buchwald and Hartwig, the N1-arylation of indoles has reached sufficient maturity for both academic and industrial applications. On the other hand, the selective C2- or C3-arylation of indoles, initiated by Ohta in the middle 1980s, has become a hot research area these last years following the reports of Sames. Surprisingly, only few reports concern the use of heterogeneous catalysts; however, the application of these emerging methodologies seems to be related to the discovery of industrially attractive systems. The direct and site-selective transition metal-catalysed N1-, C2- or C3-arylations of indoles have been the subject of almost continuous improvements since their discovery in early 1980s. This research area is mainly motivated by the biological relevance of this class of compounds in order to propose catalytic alternative syntheses to the well known methodologies involving the formation of the indole ring like the Fischer, Larock, Cacchi, Lautens etc. reactions. Since the late 1990s it has experienced new impulses related to the intensive development of catalytic C-H activation. Today, through the intensive studies of Buchwald and Hartwig, the N1-arylation of indoles has reached sufficient maturity for both academic and industrial applications. On the other hand, the selective C2- or C3-arylation of indoles, initiated by Ohta in the middle 1980s, has become a hot research area these last years following the reports of Sames. Surprisingly, only few reports concern the use of heterogeneous catalysts; however, the application of these emerging methodologies seems to be related to the discovery of industrially attractive systems. The direct and site‐selective transition metal‐catalysed N1‐, C2‐ or C3‐arylations of indoles have been the subject of almost continuous improvements since their discovery in early 1980s. This research area is mainly motivated by the biological relevance of this class of compounds in order to propose catalytic alternative syntheses to the well known methodologies involving the formation of the indole ring like the Fischer, Larock, Cacchi, Lautens etc. reactions. Since the late 1990s it has experienced new impulses related to the intensive development of catalytic CH activation. Today, through the intensive studies of Buchwald and Hartwig, the N1‐arylation of indoles has reached sufficient maturity for both academic and industrial applications. On the other hand, the selective C2‐ or C3‐arylation of indoles, initiated by Ohta in the middle 1980s, has become a hot research area these last years following the reports of Sames. Surprisingly, only few reports concern the use of heterogeneous catalysts; however, the application of these emerging methodologies seems to be related to the discovery of industrially attractive systems.
Author	Djakovitch, Laurent Joucla, Lionel
Author_xml	– sequence: 1 givenname: Lionel surname: Joucla fullname: Joucla, Lionel organization: Université de Lyon, CNRS, UMR 5256, IRCELYON, Institut de recherches sur la catalyse et l'environnement de Lyon, 2 avenue Albert Einstein, F-69626 Villeurbanne, France, Fax: (+33)-472-445-399; phone: (+33)-472-445-381 – sequence: 2 givenname: Laurent surname: Djakovitch fullname: Djakovitch, Laurent email: laurent.djakovitch@ircelyon.univ-lyon1.fr organization: Université de Lyon, CNRS, UMR 5256, IRCELYON, Institut de recherches sur la catalyse et l'environnement de Lyon, 2 avenue Albert Einstein, F-69626 Villeurbanne, France, Fax: (+33)-472-445-399; phone: (+33)-472-445-381
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Snippet	The direct and site‐selective transition metal‐catalysed N1‐, C2‐ or C3‐arylations of indoles have been the subject of almost continuous improvements since... magnified image The direct and site‐selective transition metal‐catalysed N1‐, C2‐ or C3‐arylations of indoles have been the subject of almost continuous... The direct and site-selective transition metal-catalysed N1-, C2- or C3-arylations of indoles have been the subject of almost continuous improvements since...
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SubjectTerms	arylindoles Buchwald-Hartwig amination Catalysis Chemical Sciences CH activation oxidative coupling site-selective arylation
Title	Transition Metal-Catalysed, Direct and Site-Selective N1-, C2- or C3-Arylation of the Indole Nucleus: 20 Years of Improvements
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