Nickel-Catalyzed Highly Regioselective Multicomponent Coupling of Ynamides, Aldehydes, and Silane: A New Access to Functionalized Enamides

Saito, Nozomi; Katayama, Tomoyuki; Sato, Yoshihiro

doi:10.1021/ol801534e

Cited by 95 publications

(23 citation statements)

References 65 publications

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“…Related substrates can also be obtained by hydroalumination of ynamides possessing a propargylic alcohol60c, 62 or by multicomponent nickel‐catalyzed coupling of ynamides with aldehydes and triethylsilane (Scheme ) 63. This coupling reaction occurred best when catalytic amounts of [Ni(cod) 2 ] and 1,3‐bis(2,4,6‐trimethylphenyl)imidazol‐2‐ylidene (IMes) as the ligand were used, and gave the corresponding α‐silyloxy‐enamides 85 .…”

Section: Recent Developments In the Chemistry Of Ynamides: An Oceamentioning

confidence: 99%

Ynamides: Versatile Tools in Organic Synthesis

2010

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Ynamides display an exceptionally fine balance between stability and reactivity. They also offer unique and multiple opportunities for the inclusion of nitrogen-based functionalities into organic molecules, and are emerging as especially useful and versatile building blocks for organic synthesis. Recent breakthroughs in the preparation of these substrates have revitalized interest in nitrogen-substituted alkynes, and the beginning of the 21st century has witnessed an ever-increasing number of publications reporting the development of new reactions or synthetic sequences starting from ynamides. This Review highlights major developments in this area.

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Section: Recent Developments In the Chemistry Of Ynamides: An Oceamentioning

confidence: 99%

Ynamides: Versatile Tools in Organic Synthesis

2010

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“…Recently, Sato158 reported a Ni-NHC-catalyzed multi-component coupling of ynamides, aldehydes and silanes to access functionalized enamides (Scheme 164). Reactions between ynamides 648 and various aldehydes resulted in regioselective formation of oxanickelacycle intermediate 650 , and then hydride reduction of the metallacycle by Et 3 SiH gave the desired enamides 651 in high yield with a high degree of E / Z control.…”

Section: Reactions Of Ynamidesmentioning

confidence: 99%

Ynamides: A Modern Functional Group for the New Millennium

et al. 2010

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“…The authors proposed that the ruthenium catalyst preferentially interacts with the relatively electrophilic β-carbon atom of the ynamide. [71] …”

Section: Nonmetathetic Ethylene-incorporating Ruthenium(ii)-catalymentioning

confidence: 99%

Transition‐Metal‐Catalyzed Laboratory‐Scale Carbon–Carbon Bond‐Forming Reactions of Ethylene

2013

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Ethylene, the simplest alkene, is the most abundantly synthesized organic molecule by volume. It is readily incorporated into transitionmetal–catalyzed carbon-carbon bond-forming reactions through migratory insertions into alkylmetal intermediates. Because of its D2h symmetry, only one insertion outcome is possible. This limits byproduct formation and greatly simplifies analysis. As described within this Minireview, many carbon–carbon bond-forming reactions incorporate a molecule (or more) of ethylene at ambient pressure and temperature. In many cases, a useful substituted alkene is incorporated into the product.

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Nickel-Catalyzed Highly Regioselective Multicomponent Coupling of Ynamides, Aldehydes, and Silane: A New Access to Functionalized Enamides

Cited by 95 publications

References 65 publications

Ynamides: Versatile Tools in Organic Synthesis

Ynamides: Versatile Tools in Organic Synthesis

Ynamides: A Modern Functional Group for the New Millennium

Transition‐Metal‐Catalyzed Laboratory‐Scale Carbon–Carbon Bond‐Forming Reactions of Ethylene

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