2003
DOI: 10.1002/chin.200328096
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Copper‐Catalyzed Domino Halide Exchange‐Cyanation of Aryl Bromides.

Abstract: Nitriles Nitriles Q 0520Copper-Catalyzed Domino Halide Exchange-Cyanation of Aryl Bromides. -This offers a mild, simple, and improved method for the synthesis of aromatic nitriles. -(ZANON, J.; KLAPARS, A.; BUCHWALD*, S. L.; J.

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Cited by 17 publications
(20 citation statements)
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“…Hence, low yield is obtained for aryl bromides in cyanation. Although the result is less satisfactory, we were able to obtain good yield by using iodide ion, which leads to catalysed production of aryl iodide from aryl bromide and its subsequent in situ cyanation, as reported by Buchwald et al, 74 and 0.2 mmol of KI is sufficient to promote the cyanation of aryl bromides. 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 25 26 27 28 29 30 31 32 33 34 35 36 37 38 39 40 41 42 43 44 45 46 47 48 49 50 51 52 53 54 55 56 57 58 59 60 A wide variety of diversely substituted aryl halides underwent cyanation by this procedure to produce the corresponding nitriles ( Table 2, entries 5-6) substituted aryl iodides reacted readily.…”
Section: Resultssupporting
confidence: 52%
“…Hence, low yield is obtained for aryl bromides in cyanation. Although the result is less satisfactory, we were able to obtain good yield by using iodide ion, which leads to catalysed production of aryl iodide from aryl bromide and its subsequent in situ cyanation, as reported by Buchwald et al, 74 and 0.2 mmol of KI is sufficient to promote the cyanation of aryl bromides. 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 25 26 27 28 29 30 31 32 33 34 35 36 37 38 39 40 41 42 43 44 45 46 47 48 49 50 51 52 53 54 55 56 57 58 59 60 A wide variety of diversely substituted aryl halides underwent cyanation by this procedure to produce the corresponding nitriles ( Table 2, entries 5-6) substituted aryl iodides reacted readily.…”
Section: Resultssupporting
confidence: 52%
“…After monitoring by TLC, the obtained products were isolated by EtOAc, then dried, concentrated at reduced pressure and finally recrystallized. All obtained products were well known and their structure confirmed by comparison of their mp, IR, NMR data reported by previous works [18,[34][35][36][37][38][39][40][41][42][43][44][45][46][47].…”
Section: Solventless Synthesis Of Aryl Nitrilessupporting
confidence: 61%
“…Recently, usage of ecofriendly methods to introduce nitriles has been converted to a new gate in their synthesis. Some of these challenges were reduced by ligand-free green catalytic cyanation of aryl halides using K 4 Fe(CN) 6 as an absolutely safe cyanide source [13][14][15][16][17][18]. Reports on the aldehydes cyanation in order to obtain the aryl nitriles indicated the aforementioned drawbacks of the methods [19][20][21], thus introducing economic and safe methods to obtain the aryl nitriles is of great attention.…”
Section: Introductionmentioning
confidence: 99%
“…Cyanation of aryl halides is a common and useful transformation in organic synthesis. In this reaction typical cyanide sources are KCN,61 Me 3 SiCN,62 NaCN63 and Zn(CN) 2 64. The utilization of these cyanide sources has numerous drawbacks as they are highly toxic and may contaminate the product mixture.…”
Section: Reaction Kinetics and Mechanismmentioning
confidence: 99%