Copper‐Catalyzed Bis‐ or Trifunctionalization of Alkynyl Carboxylic Acids: An Efficient Route to Bis‐ and Tris‐selenide Alkenes

Chen, Jing; Su, Shixia; Hu, Dachao; Cui, Fei‐Hu; Xü, Yanli; Chen, Yanyan; Ma, Xiangyi; Pan, Ying‐Ming; Liang, Ying

doi:10.1002/ajoc.201800086

Cited by 24 publications

(48 citation statements)

References 67 publications

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“…Some of the 5‐seleno‐triazole products obtained by this decarboxylative coupling cascade show potent inhibitory activities against human gastric cancer. The same group found that in the absence of organoazides, tris‐selenide alkenes are formed [310] . Alkynyl selenides generated from decarboxylative coupling were proposed as intermediates in both cases.…”

Section: Decarboxylative C−chalcogen Bond Formationmentioning

confidence: 96%

Decarboxylation‐Initiated Intermolecular Carbon‐Heteroatom Bond Formation

Zeng¹,

Feceu

Sivendran

et al. 2021

Adv Synth Catal

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Carboxylic acids are among the most used feedstock chemicals due to their great structural diversity and easy handling. The use of carboxylic acids and their derivatives in decarboxylative couplings has proven to be a valuable tool for the construction of C−C and C‐heteroatom bonds. This synthetic strategy provides a complementary bond disconnection to traditional cross‐coupling methods. In this review, we provide a comprehensive overview of decarboxylation‐initiated intermolecular C‐heteroatom bond formation, outlining several main mechanistic concepts combined with early examples and highlighting the achievements made in the past decade until January 2021. In these reactions, carboxylic acids and their derivatives undergo initial decarboxylation and then react with other heteroatom electrophiles and nucleophiles, thus replacing the carboxylate group with a valuable and prevalent heteroatom functionality.

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Section: Decarboxylative C−chalcogen Bond Formationmentioning

confidence: 96%

Decarboxylation‐Initiated Intermolecular Carbon‐Heteroatom Bond Formation

Zeng¹,

Feceu

Sivendran

et al. 2021

Adv Synth Catal

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“…[190] The synthesis of bis-selenide alkenes 319 and trisselenide alkenes 320 from alkynyl carboxylic acids 318 and diselenides 4 is shown in Scheme 101. [191] The reaction of alkynyl carboxylic acids 318 and diselenides 4 in the presence of CuI/Cs 2 CO 3 /toluene under white light LEDs only gave bis-selenide alkenes 319, whereas tris-selenide alkenes 320 were obtained in the presence of a CuI/Cs 2 CO 3 /NMP (N-methyl-2-pyrrolidone) system. [192][193] The synthesis of mono-selanyl alkene 321 or bisselanyl alkene 322 was successfully achieved in good yields and selectively.…”

Section: Synthesis Of Bis-and Tris-selenide Alkenementioning

confidence: 99%

Synthesis of Seleno‐Heterocycles via Electrophilic/Radical Cyclization of Alkyne Containing Heteroatoms

Sonawane

Ninomiya

et al. 2020

Adv Synth Catal

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containing heterocyclic scaffolds by virtue of their interesting reactivities and a broad range of applications in the medicinal and materials chemistry. This review involves the electrophilic/radical cyclization of alkynes containing heteroatoms which resulted into the novel Se‐heterocycles. The synthesis of seleno‐heterocycles via different nucleophiles including O, N, S, Se, Te, and C‐nucleophiles is exhaustively discussed. Also, one‐pot electrophilic cyclization of 1,3‐diynes and 1,3,5‐triynes was described in details. Furthermore, the various mechanisms underlying the synthesis of selenium‐β‐lactam, carbapenem heterocycle, bis‐ and tris‐selenide alkene, β‐selenosulfonation and selenated alkynes were discussed. The Se‐heterocycles reported in this review allow preparing these selenated compounds bearing the selenium moiety both on the rings (outside) and inside the ring (e. g. selenophenes). The review demonstrates the growing opportunities to construct selenium containing heterocycles from alkynes containing heteroatoms.

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“…This approach could nicely address the polyselenation of alkynyl carboxylic acids by avoiding the use of electrophilic diselenides. [8] Therefore, we proposed a copper-catalyzed three-component cascade coupling of alkynyl carboxylic acids, Se powder and epoxides (Scheme 1C). As a blueprint of our design, we assumed that copper-catalyzed decarboxylative selenation of alkynyl carboxylic acids with elemental selenium could generate alkynylselenylcopper species.…”

Section: Introductionmentioning

confidence: 99%

“…Given our long‐term interest in the difunctionalization of elemental selenium, [9] we aimed to find a new pathway for the alkylation of alkynylselenyl anions. This approach could nicely address the polyselenation of alkynyl carboxylic acids by avoiding the use of electrophilic diselenides [8] . Therefore, we proposed a copper‐catalyzed three‐component cascade coupling of alkynyl carboxylic acids, Se powder and epoxides (Scheme 1C).…”

Section: Introductionmentioning

confidence: 99%

“…[6] Pan et al described a three-component reaction to prepare 5-arylselanyl-1,2,3-triazoles from propiolic acids, diselenides and azides via decarboxylative selenation and subsequent intermolecular click reactions. [7] However, a prevailing challenge in copper-catalyzed decarboxylative selenation of propiolic acids with diselenides is the chemo-and region-selectivity to generate tri-selenide alkenes [8] (Scheme 1B). Thus, a new approach for transfering alkynyl carboxylic acids into C sp À Se bonds would be significant to organic synthesis and pharmaceutical science.…”

Section: Introductionmentioning

confidence: 99%

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