Copper‐Catalyzed Formation of α‐Alkoxycycloalkenones from <i>N</i>‐Tosylhydrazones

Su, Naijing; Theorell, Juliana; Wink, Donald J.; Driver, Tom G.

doi:10.1002/ange.201505993

Cited by 7 publications

(1 citation statement)

References 104 publications

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“…Copper-catalyzed reactions of diazocarbonyl compounds contribute to a number of valuable transformations in organic synthesis. [1][2][3][4][5][6][7][8] Numerous methods are known for the construction of C-C and C-X (X= N, O, S and Si) bonds using coppercarbenoids. 1 Despite these significant advances, the coppercatalyzed cross-coupling reaction of thioamides and αdiazocarbonyl compounds for the synthesis of enaminones have never been reported.…”

Section: Introductionmentioning

confidence: 99%

Copper-catalyzed chemoselective cross-coupling reaction of thioamides and α-diazocarbonyl compounds: Synthesis of enaminones

Pal

Koduri

Wang

et al. 2017

Tetrahedron Letters

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The development of operationally simple and cost-effective methods for CC bond formation reactions are highly important in pharmaceutical, agrochemical and material research. In this article we describe the first copper-catalyzed cross-coupling reaction of thioamides with acceptor/acceptor-substituted and acceptor-only substituted α-diazocarbonyl compounds to yield enaminones. The reaction shows broad substrate scope in terms of thioamides and diazocarbonyl compounds. Primary, secondary and tertiary thioamides all give enanminones when reacted with α-diazodiesters, α-diazoketoesters, α-diazodiketones, α-diazoketoamides, α-diazoesteramides, αdiazoketosulfones and α-diazomonoketones.

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Section: Introductionmentioning

confidence: 99%

Copper-catalyzed chemoselective cross-coupling reaction of thioamides and α-diazocarbonyl compounds: Synthesis of enaminones

Pal

Koduri

Wang

et al. 2017

Tetrahedron Letters

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Divergent Synthesis of Disulfanes and Benzenesulfonothioates Bearing 2‐Aminofurans From N‐Tosylhydrazone‐Bearing Thiocarbamates

Song

Mai

2017

Angewandte Chemie

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An efficient and convenient synthesis of valuable disulfanes and benzenesulfonothioates, having a 2‐aminofuran framework, has been developed by employing a copper‐catalyzed transformation of readily available N‐tosylhydrazone‐bearing thiocarbamates. This method features an inexpensive metal catalyst, mild reaction conditions, good functional‐group tolerance, short reaction times, and delivers valuable and complex products. A copper carbene generated from an N‐tosylhydrazone‐bearing thiocarbamate is proposed as the key intermediate for the transformation and it triggers the subsequent cascade. Remarkably, the Ts anion released from N‐tosylhydrazone further serves as a nucleophile, thus rendering the formation of benzenesulfonothioates under controlled conditions.

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Transition Metal Catalyzed Insertion Reactions with Donor/Donor Carbenes

et al. 2020

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Donor/donor carbenes are relatively new in the field of carbene chemistry; although applications in C−H and X−H insertion reactions are few in number, they demonstrate exquisite chemo‐ and stereo‐selectivity. Recent reports have shown that C−H, N−H, B−H, O−H, S−H, Si−H, Ge−H, Sn−H and P−H insertion reactions are feasible with a variety of transition metal catalysts, both inter‐ and intramolecularly. Furthermore, high degrees of diastereo‐ and enantioselectivity have been observed in several cases. Methods typically involve the formation of a diazo‐based carbene precursor, but procedures using diazo‐free metal carbenes have been developed with significant success. This Minireview covers transition‐metal catalyzed insertion reactions with donor/donor and donor carbenes, providing context for future developments in this emerging field.

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Copper‐Catalyzed Formation of α‐Alkoxycycloalkenones from N‐Tosylhydrazones

Cited by 7 publications

References 104 publications

Copper-catalyzed chemoselective cross-coupling reaction of thioamides and α-diazocarbonyl compounds: Synthesis of enaminones

Copper-catalyzed chemoselective cross-coupling reaction of thioamides and α-diazocarbonyl compounds: Synthesis of enaminones

Divergent Synthesis of Disulfanes and Benzenesulfonothioates Bearing 2‐Aminofurans From N‐Tosylhydrazone‐Bearing Thiocarbamates

Transition Metal Catalyzed Insertion Reactions with Donor/Donor Carbenes

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