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Synthesis and Functionalization of Indoles Through Palladium-Catalyzed Reactions Sandro Cacchi* and Giancarlo Fabrizi Dipartimento di Chimica e Technologie.

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Presentation on theme: "Synthesis and Functionalization of Indoles Through Palladium-Catalyzed Reactions Sandro Cacchi* and Giancarlo Fabrizi Dipartimento di Chimica e Technologie."— Presentation transcript:

1 Synthesis and Functionalization of Indoles Through Palladium-Catalyzed Reactions Sandro Cacchi* and Giancarlo Fabrizi Dipartimento di Chimica e Technologie del Farmaco, Sapienza, Universita di Roma, P.le A. Moro 5, Roma, Italy Chem. Rev. 2011, 111, PR215–PR283 updated 2005, 105 (7), Indole is the acronym from indigo (the natural dye) and oleum (used for the isolation) Indole ring is a structural component of a vast number of biologically active natural and synthetic compounds Classical Indole Syntheses: the Fischer indole synthesis the Gassman indole synthesis the Madelung synthesis the Bischler indole synthesis the Batcho-Leimgruber synthesis the Bartoli indole synthesis

2 Classical Indole Syntheses the Fischer indole synthesis the Gassman indole synthesis the Madelung cyclization the Bischler indole synthesis, the Batcho-Leimgruber synthesis of indoles the Bartoli indole synthesis

3 Classical Indole Syntheses the Fischer indole synthesis the Gassman indole synthesis the Madelung cyclization the Bischler indole synthesis, the Batcho-Leimgruber synthesis of indoles the Bartoli indole synthesis

4 El Premio Nobel de Química 2010 fue otorgado a los científicos Richard F. Heck (EE.UU.), Ei-ichi Negishi (Japón), y Akira Suzuki (Japón), por las reacciones de acoplamiento cruzado catalizadas por paladio en síntesis orgánica Ei-ichi NegishiAkira SuzukiRichard F. Heck

5 GENERAL STRATEGIES 1. Construction of the pyrrole ring based on the utilization, as precursors, of compounds containing nitrogen nucleophiles and carbon-carbon triple bonds 1.1. Cyclization of Alkynes: disconnection a Synthesis and Functionalization of Indoles Through Palladium-Catalyzed Reactions

6 1.1. Cyclization of Alkynes

7 1.2. Disconnection a + g

8 1.3. Disconnection a + e + g 1.4.Disconnection a + b

9 1.5. Disconnection a + d

10 1.6. Disconnection a + e (SINTESIS DE LAROCK)

11

12 1.7. Disconnection c

13 1.8. Disconnection a + f

14 GENERAL STRATEGIES 1. Construction of the pyrrole ring based on the utilization, as precursors, of compounds containing nitrogen nucleophiles and carbon-carbon triple bonds

15 GENERAL STRATEGIES 2. Construction of the pyrrole ring based on the utilization, as precursors, of compounds containing nitrogen nucleophiles and carbon-carbon double bonds 2.1. Disconnection e Synthesis and Functionalization of Indoles Through Palladium-Catalyzed Reactions

16 2.1. Disconnection e

17 2.2. Disconnection a + e 2.2. Disconnection a

18 2.3. Disconnection a 2.4. Disconnection c + h

19 GENERAL STRATEGIES 2. Construction of the pyrrole ring based on the utilization, as precursors, of compounds containing nitrogen nucleophiles and carbon-carbon double bonds Synthesis and Functionalization of Indoles Through Palladium-Catalyzed Reactions

20 GENERAL STRATEGIES 3. Construction of the pyrrole ring by C-N bond forming reactions (Buchwald /Hartwig methodologies) Synthesis and Functionalization of Indoles Through Palladium-Catalyzed Reactions 3.1. Disconnection g

21 Synthesis and Functionalization of Indoles Through Palladium-Catalyzed Reactions 3.1. Disconnection e + g 3.2. Disconnection a + g

22 Synthesis and Functionalization of Indoles Through Palladium-Catalyzed Reactions 3.3. Disconnection a + b

23 Synthesis and Functionalization of Indoles Through Palladium-Catalyzed Reactions 3.3. Disconnection a + e

24 GENERAL STRATEGIES 3. Construction of the pyrrole ring by C-N bond forming reactions Synthesis and Functionalization of Indoles Through Palladium-Catalyzed Reactions

25 GENERAL STRATEGIES 4. Functionalization of the preformed indole system Synthesis and Functionalization of Indoles Through Palladium-Catalyzed Reactions

26 GENERAL STRATEGIES 4. Functionalization of the preformed indole system Synthesis and Functionalization of Indoles Through Palladium-Catalyzed Reactions

27 GENERAL STRATEGIES 4. Functionalization of the preformed indole system Synthesis and Functionalization of Indoles Through Palladium-Catalyzed Reactions

28 GENERAL STRATEGIES 4. Functionalization of the preformed indole system Synthesis and Functionalization of Indoles Through Palladium-Catalyzed Reactions

29 GENERAL STRATEGIES 4. Functionalization of the preformed indole system Synthesis and Functionalization of Indoles Through Palladium-Catalyzed Reactions

30 GENERAL STRATEGIES 4. Functionalization of the preformed indole system Synthesis and Functionalization of Indoles Through Palladium-Catalyzed Reactions

31 Classical Indole Syntheses the Fischer indole synthesis the Gassman indole synthesis the Madelung cyclization the Bischler indole synthesis, the Batcho-Leimgruber synthesis of indoles the Bartoli indole synthesis Conclusion: In general, it is apparent from a synthetic perspective that the application of palladiumbcatalysis to indole chemistry has had a considerable impact on the synthesis of this important class of compounds. It is used almost routinely in todays preparation of a vast number of indoles, ranging from simple to complex molecular targets. Synthesis and Functionalization of Indoles Through Palladium-Catalyzed Reactions Sandro Cacchi* and Giancarlo Fabrizi Dipartimento di Chimica e Technologie del Farmaco, Sapienza, Universita di Roma, P.le A. Moro 5, Roma, Italy Chem. Rev. 2011, 111, PR215–PR28 updated 2005, 105 (7),


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