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Ouali, A.; Taillefer, M., Science of Synthesis: C-1 Building Blocks in Organic Synthesis, (2014) 2, 99.
Alkali metal cyanides, and particularly their potassium- and sodium-based representatives, have been widely used in the palladium-catalyzed cyanation of aryl iodides, bromides, and activated chlorides reported until the early 21st century.[10,11,19–25] Due to their toxicity, handling of these cyanide sources requires specific safety precautions. The success of the cyanation is ensured by the choice of an appropriate concentration of cyanide ions and often the alkali metal cyanides have to be used together with greater than stoichiometric amounts of various additives such as potassium iodide,[11] alumina,[25] 18-crown-6,[21,22] or tedious-to-prepare phase-transfer-type phosphine ligands.[31]
Me 8888, Meee eee ee-eeeeeee eeeeeeee e eeeeeeeee eeeeee eeeeeeeee e eeeeeeeeee eeee ee eeeeeeeee ee e eeee eee eeeeeee.[88] Meeeeeee eeee eeee(eeeeeeeeeeeeeeeeeeee)eeeeeeeeeee(8) (8.8 eee%) eee eee-eeee-eeeeeeeeeeeeee (8.8 eee%), eeee 8.88 eee% ee eeeeeeeeeee eeeeeeee eeeeee eee eeeeeeeeee ee eeeeeee eeeeeeeee eee eeeeeeeeeee eeee eee eeeeeee eeeeeeee 8 eeee eee eeeeeeeeeeeee eeeeeeee 8 ee eeeeeeee ee eeee eeee eeeeee eee eeeeeeeeeeeee eeeee eeee eeeeeeeeee (Meeeee 8). Meeeeeeeeee eeeeeeee eeee ee e eeeee-eeeeeeee eeeeeeee ee eeeeeee eee eeeeeee ee eee eeeeeeee. Me eee eeee ee eeeee(eeeee)eeeeee eee eeeeeeeeeeeeee, eeeee eeeeeee eeee ee Meeeeeee [8,8-eee(eeeeeeeeeeeeeeeee)-8,8-eeeeeeeeeeeeeeee] ee 8,8′-eee(eeeeeeeeeeeeeeeee)eeeeeeeee (eeee) eeee eeeeee eeeeeee.
Meeeee 8 Meeeeeeee-Meeeeeeee Meeeeeeee ee Meeeeeeee eee Meeeeeeeeeee Meee Meeeeeee eeee Meeeeeeee Meeeeee ee eee Meeeeeee ee Meeeeeeeeee Meeeeeee ee Meeeeeeeee[88]
Me8 | Meeeee (%) | Mee |
---|---|---|
8-eeeeeeee | 88 | [88] |
Me | 88 | [88] |
8-Mee | 88e | [88] |
8-MeM8M8 | 88 | [88] |
8-MM8M8 | 88 | [88] |
8-M8MM8M8 | 88 | [88] |
8-MeM8M8 | 88 | [88] |
8-MeM8MM8M8 | 88 | [88] |
8-MeMM8M8 | 88 | [88] |
8-M8MM8M8 | 88e | [88] |
8-MeM8M8 | 88 | [88] |
8-MMMM8M8M8 | 88 | [88] |
8-MeMM8M8 | 88 (88)e | [88] |
8-eeeeeee | 88e | [88] |
8-eeeeeee | 88e | [88] |
8-eeeeeeee | 88e | [88] |
e Meeeeeee eeeeee.
e 88% eeeeeeee eeee 8-eeeeeeeeeee (88 °M eee 8 e).
e 8.8 eee% Meeeeeee eeeeeee ee e-Me8M eee 8.88 eee% ee Me8MeMe.
e Meeeee ee eeeeeeeeeee ee eeeee eeeee 8.88 eee% ee Me8MeMe eeeeeee ee 8.88%.
e 8.8 eee% eeee eeeeeee ee e-Me8M.
Meee eeeeeeee, Meeeeee eee ee-eeeeeee eeeeeeee e eeeeeee eeeeeee eee eeee eeeeeeeee ee eeee eeeeeeee eeeeeeeee eee eeee eeeeeeeee eeeeee (Me/e-Me8M) eeee eeeeee eeeeeee ee eee eeeeeeeee eeeee eee eee eeeeeee ee eeee (8.8%) ee eeeeeee eeeeeee (8%) ee eeeeeeeee.[88] Meeeeeeee eee eeeeeeeee ee e eeeeeee ee eeeeeeeeeeee eee eeeeeeeeeeeeeee ee 88 °M eee 8 eeeee.
Mee eeeee eeeeeee eeeeeeeee eeeeee eeeeeeee eee eeeeeeeee ee eeee eeeeeeeee 8 eeeee eeeeeeeee eeeeeee eee eeeeeeee ee Meeeee eee ee-eeeeeee ee eee eeeee 8888e eee eeeeeeee eeeeeeeee(MM) eeeeeee ee eee eeeeeeeee eee 8,8-eee(eeeeeeeeeeeeeeeee)eeeeeee (eeeee) ee eee eeeeee (Meeeee 8).[88,88] Meee eeeeeeeeeeee eee eeeeeeee ee eee eee ee ee eeeee eeeeeeeeee eeee ee eeeeeeeeee eeeeeee eeee ee eee eeeeeeeee eeeeee eee eeee ee eeeeeee eeeeeeeeeeee ee eeeeeeeee(8) eeeeeeeee. 8,8′-Meeeeeeeeeeeeeeeeeeee (8) eee M,M,M′,M′-eeeeeeeeeeeeeeeeeeeeeeeeee eee eee eeeeeeeee eee eeeee eee eeeeeeeeeee ee e eeee eeeee ee eeeee- eee eeeeeeeeeeeeeeeeeeeee 8 eeeeeee eeeeeeee-eeeeeeeeeee ee eeeeeeee-eeeeeeee eeeeee eeeee eeee eeeeeeeeee. Meeeeeee eeee–eeee eeeeeeeeee eeeeeee eee eeee eeeeeeee eee eee eeeeee eeeeee ee eee eeeeeeeee eeeeeee eeeeee ee e eeee eeeeeeee, eeeeeeeeeeeee ee eee eeeeeeeeee eee eeeeeeeee eeee (>88%). Meee eeeeee ee eee eeeeee ee eee eeeeeeeeee, 8,8′-eeeeeeeeeeeeeeeeeeeee (8) eeeeeeeee eeeee eee eeeeee eeeeeee, eee eeeeeee eeeeeeeee M,M,M′,M′-eeeeeeeeeeeeeeeeeeeeeeeeee ee eeee eeeeeeeee ee eeeeeee eeeee, eeee ee eee eeeeeeeee ee 8-eeeeeeeeeeeee (8, Me8 = 8-MeMM8M8) ee 8-eeeeee-8-eeeeeeeeeeeeeee (8, Me8 = 8-eeeeeeeeeeeeee-8-ee). Me eeeeeeee, eeeeeeee 8,8-eee(eeeeeeeeeeeeeeeee)eeeeeee eeeeeeeee eeeeeee eee eeee eeeeeeeee eeeeeeee ee eeeeeeeee, eee eeeeee ee eee eeeeeeeee eeeeee ee eeee eeeeeeeee ee eee eeeeeeeee. Mee eeeeeee, eee eee ee 8,8-eee(eeeeeeeeeeeeeeeee)eeeeee (eeee) eeeeeeee eeeeeeeeeeee (8, Me8 = Me) ee 88% eeeee eeeeeee ee 88% eeee 8,8-eee(eeeeeeeeeeeeeeeee)eeeeeee ee eeeeeeee.
Meeeee 8 Meeeeeeee-Meeeeeeee Meeeeeeee ee Meee eee Meeeeee Meeeeeeee eeee Meeeeeeee Meeeeee ee eee Meeeeeee ee ee Meeee Meeeeeeeee[88]
Me8 | Meeee | Meeeee (%) | Mee |
---|---|---|---|
Me | 8 | 88 | [88] |
Me | 8 | 88e | [88] |
Me | MMMMM | 88 | [88] |
8-Mee | 8 | 88 | [88] |
8-Mee | MMMMM | 88 | [88] |
8-MMMM8M8 | MMMMM | 88 | [88] |
8-MeMM8M8 | 8 | 88 | [88] |
8-MeMM8M8 | MMMMM | 88 | [88] |
8-M8M-8-MeM8M8 | 8 | 88 | [88] |
8-M8M-8-MeM8M8 | MMMMM | 88 | [88] |
8,8-M8M8M8 | 8 | 88 | [88] |
8,8-M8M8M8 | MMMMM | 88 | [88] |
8-M8MM8M8 | 8 | 88 | [88] |
8-M8MM8M8 | MMMMM | 88 | [88] |
8-MeM8MM8M8 | 8 | 88 | [88] |
8-MeM8MM8M8 | MMMMM | 8 | [88] |
8M-eeeee-8-ee | 8 | 88 | [88] |
8M-eeeee-8-ee | MMMMM | eeeee | [88] |
8-eeeeeee | 8 | 88 | [88] |
8-eeeeeee | MMMMM | 88 | [88] |
8 | 88 | [88] | |
MMMMM | 88 | [88] | |
8 | 88 | [88] | |
MMMMM | 88 | [88] |
e Meeeeeeeee ee MM eeeee ee eeeeeeee eeeeeeee.
e eeee eee eeee ee eeeeee eeeeeee ee eeeee.
Meeeeeeeeeee Meeeeeeee
Meeee- eee Meeeeeeeeeeeeeeeeeeee 8; Meeeeee Meeeeeeee:[88]
MMMMMMM: Meeeeee eeeee eee ee eeeeeeee eeeeeee eee eeee eee eee eeeeeeeee eeeee.
Me e eee 88-eM eeeee eeee eeeee MMM (8.88 e, 88 eeee), MeMM (8.8 eM), eee eee eeee ee eeeeeee eeeeeee 8 (8 eeee). Mee eeeeeeeeee eee eeeeeeee (8 × eeeeee/M8 eeeeee), eee eeee e 8.88 M eeee ee Me8MeMe ee eeeeeee (8.88 eM, 8.888 eeee), 88 ee% e-Me8M ee eeeeeee (8.88 eM, 8.8 eeee), eee Me8(eee)8 (88 ee, 8.88 eeee) eeee eeeee. Mee eeeeeeeeee eee eeeeeeee (8 ×) eee eeeeeee ee eeeeeee eeeeeeeeeee eee 88 eee. Mee eeeeeee eee eeeeeeee eeeee, eee eeee eeeeee ee 88 °M eee 88 e. Mee eeeeeeee eeeeeeeeee eee eeeeeeeeee ee MMMM. Mee eeeeeee eee eeeeeee eeee MeMMe ee e-MeMMe (88 eM), eee eeee eeee eee eeeeee eeee M8M (8 × 88 eM). Mee eeeeeee eeeee eee eeeee (Me8MM8) eee eeeeeeeeeeee. Mee eeeeeee eee eeeeeeee ee eeeeee eeeeeeeeeeeeee (eeeeee eee).
Meeee- eee Meeeeeeeeeeeeeeeeeeee 8; Meeeeee Meeeeeeee:[88]
MMMMMMM: Meeeeee eeeee eee ee eeeeeeee eeeeeee eee eeee eee eee eeeeeeeee eeeee.
Mee ee eee eeeeeeeeee ee eee eeeeeeeeeeeee ee eeeeeee ee eee eeeeeee, eee eeeeee ee eee eeeeeeee eee eee eeeeeeeeeee eeee ee MMM eeeeeeeeee eee eeeeeeeeee eee eee eeeeeee ee eee eeeeeeee. MMM eee eeeee eeeee eeeeee eee eeeeee eeeee eeeee. Mee MMM eeeeeeeeeeee eeee eeeeeeee 888 ee.
Me ee MMM eeeeeeee eeee (Meeeeee), eee eeee ee eeeeeee eeeeeeee 8 (8 eeee), MMM (888 ee, 8 eeee), MMMMM ee 8 (8.8 eeee), Me(MMe)8 (8 ee, 8.88 eeee), eeeee (88.8 ee, 8.88 eeee), eee eeeeeee (8 eM) eeee eeeeeee eeeee eeeee ee 888 °M eee 88 e. Meeee eeeeeee, eeeeeeeeee eeeeee eeeeeee eeeee (eeeeeeee eeeeeeee) eee eeeee, eee eee eeeeeee eee eeeeeee eeee MM8Me8 (8 eM) eee eeeeee eeee M8M (8 eM). Mee eeeeeee eeeee eee eeeee (Me8MM8) eee eeeeeeee ee MM. Meeeeeee eeee eeeeeeee ee eeeeee eeeeeeeeeeeeee.
References
[10] | Meeeee, M.; Meeeeee, M.; Meeeeeeeee, M.; Mee, M., Meee. Meee., (8888), 888. |
[11] | Meeeee, M.; Meeeeee, M.; Meeeeeeeee, M.; Meee, M.; Mee, M.; Meeeee, M., Meee. Meee. Mee. Mee., (8888) 88, 8888. |
[19] | Meeeee, M.; Meeeeeee, M., Meee. Meee., (8888), 888. |
[21] | Meeeeáeee, M.; Šeeeeý, M., Meeeeee. Meeee. Meee. Meeeee., (8888) 88, 8888. |
[22] | Meee, M.; Meeeee, M., M. Meeeeeeeee. Meee., (8888) 88, 8888. |
[25] | Meeeee, M. M.; Meeee, M. M., M. Mee. Meee., (8888) 88, 8888. |
[31] | Meeee, M.; Meeeeee, M.; Meee, M., Meeeeee, (8888), 888. |
[32] | Meee, M.; Meeeeeee, M. M., Mee. Meee., (8888) 8, 8888. |
[33] | Meeeee, M. M.; Meeeeee, M. M., M. Me. Meee. Mee., (8888) 888, 88888. |
[34] | Meeeeeeeeee, M.; Meee, M.; Meeeee, M.; Meee, M., Meeeeeeeeee Meee., (8888) 88, 8888. |
[35] | Meeeeeeeeee, M.; Meee, M.; Meeeeee, M.; Meeeeee, M.; Meee, M.; Meeee, M.; Meeeee, M., Meee.–Mee. M., (8888) 8, 8888. |