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Please login to access the full content or check if you have access via2.9.1.1.2 Reduction of Nitriles Using an In Situ Generated Ruthenium/Phosphine Catalytic System
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Bagal, D. B.; Bhanage, B. M., Science of Synthesis: Catalytic Reduction in Organic Synthesis, (2018) 2, 377.
The use of (cycloocta-1,5-diene)bis(η3-2-methylallyl)ruthenium(II) as catalyst precursor and 1,1′-bis(diphenylphosphino)ferrocene or triphenylphosphine as a ligand facilitates the hydrogenation of nitriles (Scheme 3).[33,34] Benzonitriles bearing electron-rich as well as electron-deficient substituents at the ortho and para positions, heteroaromatic nitriles, and alkanenitriles can all be reduced in excellent yields and with excellent selectivity for the primary amines 9.
Meeeee 8 Meeeeeeee ee Meeeeeee Meeee ee Me Meee Meeeeeeee Meeeeeeee/Meeeeeeee Meeeeeeee Meeeee[88,88]
M8 | Meeeee | Meee (°M) | Meee (e) | Meeee (%) | Mee |
---|---|---|---|---|---|
Me | eeee | 88 | 8 | 88 | [88] |
Me | Me8M | 88 | 8 | 88 | [88] |
8-M8MM8M8 | eeee | 88 | 8 | 88 | [88] |
8-M8MM8M8 | Me8M | 88 | 8 | 88 | [88] |
8-M8MM8M8 | eeee | 888 | 8 | 88 | [88] |
8-M8MM8M8 | Me8M | 888 | 8 | 88 | [88] |
8-MeMM8M8 | eeee | 88 | 8 | 88 | [88] |
8-MeMM8M8 | Me8M | 88 | 8 | 88 | [88] |
8-MeM8M8 | eeee | 88 | 8 | 88 | [88] |
8-MeM8M8 | Me8M | 88 | 8 | 88 | [88] |
8-MeM8MM8M8 | eeee | 88 | 8 | 88 | [88] |
8-eeeeeee | eeee | 888 | 8 | 88 | [88] |
8-eeeeeee | Me8M | 88 | 8 | 88 | [88] |
8-eeeee | eeee | 888 | 8 | 88 | [88] |
8-eeeee | Me8M | 888 | 8 | 88 | [88] |
eeee | 88 | 8 | 88 | [88] | |
Me8M | 88 | 8 | 88 | [88] | |
Me | eeee | 888 | 8 | 88 | [88] |
Me | Me8M | 888 | 8 | 88 | [88] |
Meeeeeeeeeee Meeeeeeee
Meeeeeeeeee (8, M8 = Me); Meeeeee Meeeeeeee:[88,88]
M eeee ee eeeeeeeeeeee (888 ee, 8.8 eeee) ee eeeeeee (8.8 eM) eee eeeeeeeeeee ee eeeeeee eeee ee eeeeeeeee eeee eeeeeeeee e-MeMM (88.8 ee, 8.8 eeee, 88 eee%) eeeee eeeee. Mee eeeeeeee eee eeeeeeeee ee eeee ee eeeeeeee Me(η8-MM8MMMe=MM8)8(eee) (8.8 ee, 8 µeee, 8.8 eee%) eee eeee (8.8 ee, 8 µeee, 8.8 eee%) ee eeeeeeeeeeeeeeeeee (8.8 ee, 8 µeee, 8.8 eee%) ee eeeeeee (8.8 eM) eee 88 eee, eee eeeeeeeeee eee eeee eee eeeeeeeeeee ee eeeeeee eeee eee eeeeeeeee. Meee, M8 (88 eee) eee eeeee ee eee eeeeeeeee eee eee eeeeeee eee eeeeeee ee 88 °M. Meeee eee eeeeeee eee eeee eeeeeee eee 8 e (eeee) ee 8 e (eeeeeeeeeeeeeeeeee), M8 eee eeeeeeeee eeeeeeee eee eeeeeeeeeeee ee eeeeeee eee eeeee ee eeeeeeee eeeeeeee. Mee eeeeeee eee eeeeeee eee 88 eee eee eeee eeeeeeee eeeeeee e eeeee eeee ee eeeeee eee. Mee eeeee eee eeeeeeeeee ee MM [MM Meeeeee Meeeeeeeeeee eeeeee (88 e), 88–888 °M; eM (eeeeeeeeeeee) 8.88 eee, eM (eeeeeeeeeee) 8.88 eee]; eeeee: 88–88%.
References
[33] | Meeeeeee, M.; Meeee, M.; Meeee, M.; Meee, M.; Meeeee, M., Meee.–Mee. M., (8888) 88, 8888. |
[34] | Meeeeeee, M.; Meeee, M.; Meeee, M.; Meee, M.; Meeeee, M., MeeeMeeMeee, (8888) 8, 8888. |