Gold‐Catalyzed Intermolecular [4+2] Annulation of 2‐Ethynylanilines with Ynamides: An Access to Substituted 2‐Aminoquinolines

Zhao, Ximei; Song, Xinlong; Jin, Hongming; Zeng, Zhongyi; Wang, Qian; Rudolph, Matthias; Röminger, Frank; Hashmi, A. Stephen K.

doi:10.1002/adsc.201800341

Cited by 35 publications

(16 citation statements)

References 72 publications

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“…Over the last 5–6 years, several reports on the carboamination of ynamides have been described. Pyrimidines, tetrahydropyrimidines, dihydroisoquinolines, and quinolines − have all been synthesized using carboamination chemistry (Scheme ). The group of Liu described the formal [2 + 2+2] cycloaddition toward the syntheses of pyrimidines 94 using ynamides 92 and nitriles 93 .…”

Section: Carbon π-Systems With Electron-donating Groupsmentioning

confidence: 91%

Gold-Catalyzed Reactions of Specially Activated Alkynes, Allenes, and Alkenes

et al. 2020

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This review describes the gold-catalyzed reactions of specially activated alkynes, allenes, and alkenes. Such species are characterized by the presence of either electron-donating or electron-withdrawing groups as substituents of the carbon π-system. They are intrinsically polarized, and when compared to their nonspecially activated counterparts can therefore be involved in gold-catalyzed transformations featuring increased regio-, stereo-, and chemoselectivities. The chemistry of specially activated carbon π-systems under homogeneous gold catalysis is extremely rich and varied. The reactivity observed with nonspecially activated unsaturated systems can often be transposed to specially activated ones without loss of efficiency. However, specially activated carbon π-systems also exhibit specific reactivities that cannot be attained with regular substrates. In this family of carbon π-systems, ynamides and their analogs, along with alkynyl carbonyl derivatives, are the classes of substrates that have retained the most attention. This review provides an overview of the chemistry developed with all classes of specially activated carbon π-systems by discussing their general and specific reactivities, presenting and commenting on their gold-catalyzed transformations as well as their applications.

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Section: Carbon π-Systems With Electron-donating Groupsmentioning

confidence: 91%

Gold-Catalyzed Reactions of Specially Activated Alkynes, Allenes, and Alkenes

et al. 2020

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“…There are few examples using inexpensive late-transition-metals such as nickel as the catalyst in the hydroamination of alkynes, and the reported reactions usually require harsh reaction conditions and limited scope . Only a few reports on metal-catalyzed intermolecular hydroamination or amination/cyclizations of ynamides with anilines are known, and most of the studies rely on gold-based systems via α-addition (e.g., Scheme c). In this paper, we describe a nickel-catalyzed cyclization of ynamide-nitriles with primary anilines involving β-regioselective addition, which provides an efficient and attractive route for the synthesis of highly functionalized 3-aminoindoles and 4-aminoisoquinolines (Scheme d).…”

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confidence: 99%

Nickel-Catalyzed β-Regioselective Amination/Cyclization of Ynamide-Nitriles with Amines: Synthesis of Functionalized 3-Aminoindoles and 4-Aminoisoquinolines

Xie

Gan

et al. 2021

Org. Lett.

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“…[1,2] Further activation of ynamides often relies on their reaction with Brønsted [3] or transition metal pacids [4] to form keteniminium ions [1a, 5] providing superb reactivity within addition and/or annulation processes. Such approaches were particularly realized in the emerging gold catalysis of ynamides [6] leading to indoles [7,8] and quinolines [9,10] with different substitution pattern. Protocols aiming at generating reactive neutral ketenimines [11] from ynamides have been less explored.…”

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confidence: 99%

Media‐Driven Pd‐Catalyzed Reaction Cascades with 1,3‐Diynamides Leading Selectively to Either Indoles or Quinolines

et al. 2021

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Divergent Pd-catalyzed reaction cascades with various 1,3-diynamides yielding either 2-amino-3-alkynylindoles or 2-amino-4-alkenylquinolines were established. Omitting or adding TBAF (tetrabutylammonium fluoride) to the reaction of N,N-(2-iodophenyl)(4-toluenesulfonyl)-1,3diynamides with secondary or primary amines in the presence of KOH in THF and catalytic amounts of Pd(PPh 3 ) 4 completely changed the outcome of the reaction. In the absence of TBAF, 2-amino-3-alkynylindoles were the sole products, while the presence of TBAF switched the product formation to 2-amino-4-alkenylquinolines. Deuterium labeling proceeded selectively at the C3 and C11 positions of the 2-amino-4alkenylquinoline products and this suggests the unprecedented formation of [4]cumulenimines from 1,3-diynamides as reactive key intermediates.

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Gold‐Catalyzed Intermolecular [4+2] Annulation of 2‐Ethynylanilines with Ynamides: An Access to Substituted 2‐Aminoquinolines

Abstract: A gold‐catalyzed intermolecular [4+2] annulation of easily accessible 2‐ethynylanilines with ynamides offers a highly region‐selective, modular, efficient, and atom‐economical strategy for the synthesis of substituted 2‐aminoquinolines in up to 93% yield.magnified image

Cited by 35 publications

References 72 publications

Gold-Catalyzed Reactions of Specially Activated Alkynes, Allenes, and Alkenes

Gold-Catalyzed Reactions of Specially Activated Alkynes, Allenes, and Alkenes

Nickel-Catalyzed β-Regioselective Amination/Cyclization of Ynamide-Nitriles with Amines: Synthesis of Functionalized 3-Aminoindoles and 4-Aminoisoquinolines

Media‐Driven Pd‐Catalyzed Reaction Cascades with 1,3‐Diynamides Leading Selectively to Either Indoles or Quinolines

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