Update 1 of: Synthesis and Functionalization of Indoles Through Palladium-Catalyzed Reactions

Cacchi, Sandro; Fabrizi, Giancarlo

doi:10.1021/cr100403z

Cited by 670 publications

(171 citation statements)

References 592 publications

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“…C-H bonds of electron-rich aromatic amides showed better activity [102]. Chatani and co-workers found that utilizing a bidentate system, aromatic amides having a pyridin-2-ylmethylamine moiety could undergo cyclocarbonylation through C-H bond activation in the presence of catalytic amount of Ru 3 (CO) 12 and CO (Scheme 34b). Phthalimides were obtained in moderate to good yields.…”

Section: Synthesis Of Five-membered Heterocycles Via Oxidative Carbonmentioning

confidence: 99%

Synthesis of Functionalized Heterocycles via Oxidative Carbonylation

Xing

2015

Topics in Heterocyclic Chemistry

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With the assistance of a proper oxidant, carbonylation of two nucleophiles can take place directly in carbonylation conditions, which is defined as oxidative carbonylation. This process starts with the reaction of nucleophiles with the metal catalyst in oxidation state (M (n + 2) ), followed by insertion of CO and subsequent reductive elimination, providing the carbonylated products and the metal catalyst in reduction state (M (n) ). The oxidant could reoxidize M (n) to M (n + 2) to promote the catalytic cycle. Oxidative carbonylation avoids the difficult oxidative addition of R-X to metal catalyst, so this kind of carbonylation could proceed in mild conditions. What's more is that oxidative carbonylation doesn't need prefunctionalization of substrates. So, it's no wonder that considerable attention has been drawn to construct important carbonylated compounds through oxidative carbonylation. Particularly, much progress in synthesis of carbonylated heterocycles via oxidative carbonylation has been achieved in the past decades. Here, we summarized the main achievements in this area from 1982 to the beginning of 2015.

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Section: Synthesis Of Five-membered Heterocycles Via Oxidative Carbonmentioning

confidence: 99%

Synthesis of Functionalized Heterocycles via Oxidative Carbonylation

Xing

2015

Topics in Heterocyclic Chemistry

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“…There are various synthetic routes for the preparation of indole derivatives, such as Fischer indole synthesis [32], Bartoli indole synthesis [31] or Pd/Cu-catalyzed cyclization [42,43]. Previously, we reported the preparation of indole bearing pendant functionalities using the Sonogashira reaction followed by Zn-mediated cyclization [28].…”

Section: Preparations Of Ligand Precursors and Magnesium Complexesmentioning

confidence: 99%

Magnesium Pyrazolyl-Indolyl Complexes as Catalysts for Ring-Opening Polymerization of L-Lactide

Chen¹,

Lin²,

Peng³

2015

Polymers

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A series indole-based ligand precursors, Pz R IndH (R = H, Pz H IndH; R = Me, Pz Me IndH; R = t-Bu, Pz tBu IndH; and R = Ph, Pz Ph IndH), have been synthesized via copper-catalyzed N-arylation (for Pz H IndH) or the Bartoli indole synthesis (for Pz Me IndH, Pz tBu IndH and Pz Ph IndH) reactions with moderate to high yield. Reactions of these ligand precursors with 0.7 equivalent of Mg n Bu 2 in THF (for 1) or hexane (for 2-4) afforded the bis-indolyl magnesium complexes 1-4, respectively. All the ligand precursors and related magnesium complexes have been characterized by NMR spectroscopy and elemental analyses. The molecular structure is reported for compound 1.These novel magnesium complexes demonstrate efficient catalytic activities for the ring-opening polymerization of L-lactide in the presence of alcohol.

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“…In this context, palladium catalysis has revolutionized modern indole synthesis, with the vast majority of now-established synthetic protocols involving assembly of the pyrrole ring fragment by use of combinations of nitrogen nucleophiles and alkyne synthons. [8][9][10] Notwithstanding the utility of such methods, the development of efficient new routes to indoles that make use of alternative disconnection strategies and source materials remains an important goal in the quest to diversify inroads to these important heterocycles. Of particular interest are new syntheses that accommodate inexpensive and structurally variable substrate classes within one-pot, multicomponent reactions, [11,12] ideally without the requirement of inert atmosphere reaction conditions.…”

Section: Introductionmentioning

confidence: 99%

Utilizing Mor‐DalPhos/Palladium‐Catalyzed Monoarylation in the Multicomponent One‐Pot Synthesis of Indoles

et al. 2014

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Abstract:The application of a Mor-DalPhos/palladium catalyst system in the one-pot, multicomponent assembly of substituted indoles from ortho-chlorohaloarenes, alkyl ketones (including acetone), and primary amines is reported. The described protocols offer improved substrate scope in all three reaction components, under more mild conditions and without the need for an additional drying agent. Also reported are the first examples of such multicomponent reactions where all reactants are combined at the start of the reaction, without the need for inert atmosphere reaction conditions.

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Update 1 of: Synthesis and Functionalization of Indoles Through Palladium-Catalyzed Reactions

Abstract: |Chem. Rev. 2011, 111, PR215-PR283Chemical Reviews REVIEW Finally, one can reasonably anticipate that future studies will provide new applications to the preparation of complex molecules, particularly in the area of biologically active compounds.

Cited by 670 publications

References 592 publications

Synthesis of Functionalized Heterocycles via Oxidative Carbonylation

Synthesis of Functionalized Heterocycles via Oxidative Carbonylation

Magnesium Pyrazolyl-Indolyl Complexes as Catalysts for Ring-Opening Polymerization of L-Lactide

Utilizing Mor‐DalPhos/Palladium‐Catalyzed Monoarylation in the Multicomponent One‐Pot Synthesis of Indoles

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