One‐Pot Multi‐Component Synthesis of Triarylacrylonitriles Directly by Using CaC₂ as a Concise Acetylene Source and K₄[Fe(CN)₆] as an Eco‐Friendly Cyanide Source

Abstract

An efficient method for the one‐pot multicomponent synthesis of triarylacrylonitriles from various aryl iodides directly by using calcium carbide as a concise acetylene source and potassium hexacyanoferrate(II) as an eco‐friendly cyanide source is described. This protocol benefits from safe, inexpensive and easy‐to‐handle starting materials, good substrate tolerance and simple work‐up procedure.

Calcium‐Based Sustainable Chemical Technologies for Total Carbon Recycling

“…For example, it is possible to stop the reaction after the first coupling by restricting the amount of calcium carbide; thus producing terminal alkynes. The addition of an inorganic source of cyanide (K 4 [Fe(CN) 6 ]) to the mixture leads to the second addition step and synthesis of 2,3,3‐triarylacrylonitriles . The formation of aryl alkyne/bis‐arylalkyne mixtures is also possible.…”

“…The additiono fa ni norganic source of cyanide( K 4 [Fe(CN) 6 ]) to the mixture leads to the second addition step and synthesis of 2,3,3-triarylacrylonitriles. [88] The formationo fa ryl alkyne/bis-arylalkyne mixtures is also possible. Additionally,i ti sp ossible to replacea ryl iodide with boronic acids [89] and aryl bromides: [90] the same bis-arylalkynes are formed.…”

Palladium‐Catalyzed One‐Pot Four‐Component Synthesis of β‐Cyano‐α,β‐unsaturated Ketones Using Calcium Carbide as an Acetylene Source and Potassium Hexacyanoferrate(II) as an Eco‐Friendly Cyanide Source

“…The product (Z)-4-oxo-2,4-diphenylbut-2-enenitrile (3 a) was obtained in 45% yield (Table 1, entry 1). COMMUNICATIONS asc.wiley-vch.de desired product (entries [13][14][15][16]. [9a,10] The reaction yield could be improved in the presence of some ligands such as PPh 3 , dppe, dppp and dppb (entries 2-5).…”

“…Recently, K 4 [Fe(CN) 6 ] has been used as an eco-friendly cyanide source for some organic reactions to synthesize important compounds bearing cyano groups. [13] Our recent research interests focused on the use of CaC 2 and K 4 [Fe(CN) 6 ] in the organic synthesis, respectively, and reported the synthesis of 2-methylbenzofurans, [14] diarylacetylenes, [15] triarylacrylonitriles [16] and 1,3,5-triaroylcyclohexanes [17] direct using CaC 2 as an acetylene source, and the cyanation of unsaturated compounds including C=O, C=N and/or C=C bonds by nucleophilic addition reactions using K 4 [Fe(CN) 6 ] as an eco-friendly cyanide source. [18] In this work, we report a more efficient and green method for the combined use of two cheap and safe inorganic chemicals, CaC 2 as an easy-to-handle acetylene source and K 4 [Fe(CN) 6 ] as an eco-friendly cyanide source, in one reaction to synthesize β-cyanoα,β-unsaturated ketones by one-pot four-component procedure using commercial available aryl halides and aroyl chlorides as substrates.…”

“…Some inorganic bases, such as Cs 2 CO 3 , K 2 CO 3 , Na 2 CO 3 , KOAc and NaOH, exhibited moderate to good activities for the reaction (entries 5, [9][10][11][12]. In contrast, organic bases, such as Et 3 N, DBU, DMAP and DABCO, could not give the desired product (entries [13][14][15][16]. The best yield for 3 a was obtained by using K 2 CO 3 as a base (entry 9).…”