Copper-catalyzed domino synthesis of ynamines

Rao, Maddali L. N.; Islam, Sk Shamim; Dasgupta, Priyabrata

doi:10.1039/d1ob01383a

Cited by 4 publications

(2 citation statements)

References 35 publications

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“…[22] Even though the synthesis of ynamides is well documented, compounds bearing more than two ynamides (or ynamines) remain scarce. [23][24][25][26] We recently synthesized a tris-ynamide (1) conjugated to a triphenylamine and reacted it with TCNE to access compound 2 bearing three TCBD units (Figure 1a). [27] In order to go a step further, we wish to challenge the incorporation of four TCBD units derived from ynamides onto a single aromatic compound.…”

Section: Introductionmentioning

confidence: 99%

“…We are particularly interested in these TCBDs for their original optoelectronic properties, [19] and have thus been working on the conjugation of ynamides to π‐systems, [20,21] which can pose a challenge when it comes to introducing two ynamide functions within the same molecule [22] . Even though the synthesis of ynamides is well documented, compounds bearing more than two ynamides (or ynamines) remain scarce [23–26] …”

Section: Introductionmentioning

confidence: 99%

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Quadruple Functionalization of a Tetraphenylethylene Aromatic Scaffold with Ynamides or Tetracyanobutadienes: Synthesis and Optical Properties

et al. 2022

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Ynamides are useful and versatile building blocks in organic synthesis, from which 1,1,4,4‐tetracyanobutadienes (TCBD) can be prepared for application in molecular electronics. However, their insertion onto multi‐functional molecular scaffold remains a synthetic challenge. In this work, we report the two‐steps synthesis in good isolated yield (64 % overall, 89 % stepwise) of a tetraphenylethylene (TPE) bearing four ynamides, and its further one‐step conversion into the tetra‐TCBD derivative through a [2+2] cycloaddition‐retroelectrocyclization sequence. The concomitant formation of the four ynamides required a specific optimisation of the reaction conditions. Although a poor fluorescent emitter in solution, the tetra‐TCBD compound displayed near‐infrared luminescence in the solid state, which is an attractive optoelectronic feature when considering future applications in molecular electronic devices.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Quadruple Functionalization of a Tetraphenylethylene Aromatic Scaffold with Ynamides or Tetracyanobutadienes: Synthesis and Optical Properties

et al. 2022

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CuI/DMAP‐Catalyzed Oxidative Alkynylation of 7‐Azaindoles: Synthetic Scope and Mechanistic Studies

Talukdar,

Mondal,

Kumar Dhaked

et al. 2024

Chemistry An Asian Journal

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An efficient and practical method for the N‐alkynylation of 7‐azaindoles has been established by using CuI/DMAP catalytic system at room temperature and in open air. This simple protocol has been successfully employed in the synthesis of a wide range of N‐alkynylated 7‐azaindoles with good yields. Also, this approach is well‐suited for large‐scale N‐alkynylation reactions. The designed N‐alkynylated 7‐azaindoles were further subjected to Cu‐/Ir‐catalyzed alkyne−azide cycloaddition (CuAAC/IrAAC) or “click” reaction for the rapid synthesis of 1,4‐/1,5 disubstituted 1,2,3‐triazole decorated 7‐azaindoles. A mechanistic study based on density functional theory (DFT) calculations and ultraviolet−visible (UV) spectroscopic studies revealed that the CuI and DMAP combination formed a [CuII(DMAP)2I2] species, which acts as an active catalyst. The DFT method was used to assess the energetic viability of an organometallic in the C‐N bond formation pathway originating from the [CuII(DMAP)2I2]complex. We expect that the newly designed Cu/DMAP/alkyne system will offer valuable insights into the field of Cu‐catalyzed transformations.

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Five-membered ring systems: pyrroles and benzo analogs

Lopchuk

2023

Progress in Heterocyclic Chemistry

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Copper-catalyzed domino synthesis of ynamines

Abstract: A Cu-catalyzed domino protocol using gem-dibromoalkenes and N-heteroarenes is developed for the synthesis of ynamines and it is applied in the synthesis of enynamines, bis/tris-ynamines and peyonine natural product.

Cited by 4 publications

References 35 publications

Quadruple Functionalization of a Tetraphenylethylene Aromatic Scaffold with Ynamides or Tetracyanobutadienes: Synthesis and Optical Properties

Quadruple Functionalization of a Tetraphenylethylene Aromatic Scaffold with Ynamides or Tetracyanobutadienes: Synthesis and Optical Properties

CuI/DMAP‐Catalyzed Oxidative Alkynylation of 7‐Azaindoles: Synthetic Scope and Mechanistic Studies

Five-membered ring systems: pyrroles and benzo analogs

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