Palladium-Catalyzed Three-Component Coupling of Ynamides

Wakamatsu, Hideaki; Takahashi, Ayano; Ishii, Ayaka; Kikuchi, Yoshihiro; Sasaki, Masashi; Saito, Yukako; Natori, Yoshihiro; Yoshimura, Yuichi

doi:10.1021/acs.orglett.0c01426

Cited by 8 publications

(2 citation statements)

References 34 publications

(13 reference statements)

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“…Recent research has demonstrated the successful use of a combination of iodoarenes 7 and aryl/alkenyl boronic acids 3 in the dicarbofunctionalization of ynamide under Pd‐catalyst (Yoshimura and team in 2020, Scheme 3). [15] A direct aryl‐palladation of ynamide 1 a at first forms α‐aryl‐vinyl‐Pd species 8 a . Next, the trapping of 8 a with aryl boronic acids gives 8 (Scheme 3).…”

Section: Difunctionalization Of Ynamidesmentioning

confidence: 99%

Regioselective Difunctionalization and Annulation of Ynamide

2023

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The use of ynamides in organic synthesis has gained significant attention due to their ability to provide access to complex molecular structures through transformations such as 1,2-difunctionalization and annulation reactions. These reactions enable the formation of highly functionalized N-bearing olefins and unusual N-bearing heterocycles. In this minireview, we present a systematic overview of the regioselective difunctionalization and annulation reactions of ynamides. We discuss the multi-component reactions, and radical-triggered functionalizations across the ynamides carbon-carbon multiple bonds and the use of bifunctional reagents in annulation of ynamides, highlighting their potential in expanding the substrate scope. Furthermore, we provide insights into the mechanistic breakthroughs that have been achieved in recent years in the development of these reactions. Finally, we emphasize the promising future prospects of ynamides as versatile building blocks for the synthesis of complex molecular architectures.

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Section: Difunctionalization Of Ynamidesmentioning

confidence: 99%

Regioselective Difunctionalization and Annulation of Ynamide

2023

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“…1a). 41 It is imperative to note that a significant focus on the threecomponent unsymmetrical dicarbofunctionalization of ynamides has been realized in recent years. While the two-component difunctionalization of ynamides are mostly referred to annulation 42 (Fig.…”

Section: Introductionmentioning

confidence: 99%

Two-component symmetrical diarylation of ynamides

2023

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Stepwise Suzuki−Miyaura Cross‐Coupling of Triborylalkenes Derived from Alkynyl−B(dan)s: Regioselective and Flexible Synthesis of Tetrasubstituted Alkenes

et al. 2020

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Alkenes with three boryl groups of differing reactivities were synthesized and subsequently cross‐coupled regioselectively with aryl halides in a stepwise manner to afford tetrasubstituted alkenes. The key triborylalkene is derived from the platinum‐catalyzed diboration of alkynyl−B(dan)s with B2(pin)2. Due to excellent regioselectivity and reaction efficiency of each step starting with alkynyl−B(dan)s, tetrasubstituted alkenes with desired carbon frameworks at desired positions can be prepared in high yields. For example, an alkene with four distinct aryl groups, p‐MeOC6H4, p‐CF3C6H4, p‐MeC6H4, and p‐NCC6H4, was obtained in 71% overall yield via six steps, starting with the dehydrogenative borylation of p‐MeC6H4C≡CH with HB(dan). Moreover, a variety of tetrasubstituted alkenes, including regio‐ and stereoisomers of the above tetraarylalkene, AIE‐active TPTPE and derivatives thereof, and (Z)‐tamoxifen, a well‐known breast cancer drug, were accessed via the developed strategy.

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Palladium-Catalyzed Three-Component Coupling of Ynamides

Cited by 8 publications

References 34 publications

Regioselective Difunctionalization and Annulation of Ynamide

Regioselective Difunctionalization and Annulation of Ynamide

Two-component symmetrical diarylation of ynamides

Stepwise Suzuki−Miyaura Cross‐Coupling of Triborylalkenes Derived from Alkynyl−B(dan)s: Regioselective and Flexible Synthesis of Tetrasubstituted Alkenes

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