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2.9.1.3.3 Hydrogenation of Nitriles Using Iron Complexes

DOI: 10.1055/sos-SD-227-00186

Bagal, D. B.; Bhanage, B. M.Science of Synthesis: Catalytic Reduction in Organic Synthesis, (20182387.

An iron complex 28, bearing a dibenzylamine type PNP ligand, has been used for the selective reduction of (het)aryl, benzylic, and aliphatic nitriles to primary amines using hydrogen gas at elevated temperatures, in the presence of potassium hexamethyldisilazanide and sodium triethylborohydride (Scheme 13).[‌45‌] Various (het)aryl, benzylic, and aliphatic nitriles are effectively converted into the corresponding primary amines 29.

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M8 Meeeeeee (eee%) Meee (e) Meeeee (%) Mee
Me 8 88 88 [‌88‌]
8-MeMM8M8 8 88 88 [‌88‌]
8,8-(MeM)8M8M8 8 88 88 [‌88‌]
8-MM8M8 8 88 88 [‌88‌]
8-MeM8M8 8 88 88 [‌88‌]
8-eeeeeee 8 88 88 [‌88‌]
8-MeeMM8 8 88 88 [‌88‌]
8,8-(MeM)8M8M8MM8 8 88 88 [‌88‌]
(MM8)8Me 8 88 88 [‌88‌]
Me 8 88 88 [‌88‌]

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Meeeeeeeeee 88

M8 Meee (°M) Meeee (%) Mee
Me 88 88 [‌88‌]
8-e-MeM8M8 88 88 [‌88‌]
8-MeMM8M8 888 88e [‌88‌]
8-MeMM8M8 888 88 [‌88‌]
8-M8MM8M8 888 88 [‌88‌]
8-MeM8M8 888 88 [‌88‌]
8-MeM8M8 888 88 [‌88‌]
8-eeeeeee 888 88 [‌88‌]
8-MeM8MM8M8 888 88 [‌88‌]
8-MeMMM8M8 888 88 [‌88‌]
8-eeeeeee 888 88 [‌88‌]
8-eeeeeee 888 88 [‌88‌]
(MM8)8Me 88 88e [‌88‌]
Me 88 88 [‌88‌]
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(MM8)8Me 88 88 [‌88‌]
(MM8)88Me 88 88 [‌88‌]
(MM8)88Me 88 88 [‌88‌]
Me 88 88 [‌88‌]
(MM8)8Me 88 88 [‌88‌]
(M)-MM=MMMe 88 88 [‌88‌]
8-MeMM8M8MM8 88 88 [‌88‌]

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Meeeee 88 Meeeeeeee ee Meeeeeeeee Meeee ee Meee–MMM Meeeee Meeeeee[‌88‌]

Meeeeeeeeee 88

M Meeee (%) Mee
(MM8)8 88 [‌88‌]
(MM8)8MM(Me) 88 [‌88‌]
88 [‌88‌]

Meeeeeeeeeee Meeeeeeee

Meeeeeeeeee (88, M8 = Me); Meeeeee Meeeeeeee:[‌88‌]

Mee Me eeeeeee 88 (8.8 ee, 8.88 eeee, 8 eee%) eee eeeeeeeee ee MMM (8 eM) eee e 8 M MMM eeee ee MeMMe8M (88 µM, 8.88 eeee, 8 eee%) ee MMM (8 eM) eee eeeee eeeeeeee ee ee eeeee eee eeeeeee eee eeeeeee. Mee eeeeeee eee eeeeeee eee 88 eee, eee eee eeeeeee eee eeeeeeeeee eeeee eeeeeee eeeeeeee. MMMMM (8.8 ee, 8.88 eeee, 8 eee%) eee eeeeeeeeeeee (888 ee, 8 eeee) eeee eeeee ee eee eeeeeee eee eee eeeeeee eee eeeeeeeee ee MMM (8 eM) eee eeeeee ee e eeee-eeeeeeee eeeeeeeee. Mee eeeeeeeee eee eeeeeeeeeee eeee M8 (88 eee) eee eeeeee ee 888 °M (eeee eeeeeeeeeee) eeee eeeeeeee eee 88 e. Mee eeeeeee eee eeee eeeeee ee ee eee eeeeee M8 eee eeeeee eee eeeeeeeee. Mee eeeeeee eee eeeeeeee ee MM/MM ee 8M MMM eeeeeeeeeeee eeeee e-eeeeee ee eeeeeee ee eeeeeeee eeeeeeee; eeeee: 88%.

Meeeeeeeeee Meeeeeeeeeeee (88, M8 = Me); Meeeeee Meeeeeeee:[‌88‌]

Meeee eeeee, e 8-eM eeeee eeee eeeeeeee eeee e eee, eeeeee, eeeeee, eee eeeeeee eee eee eeeeeee eeee Me eeeeeeee 88 (8.8 ee, 8 µeee, 8 eee%), eeeee eee eeeeeee eeee eeeeeeee eMeMM (8 eM). Meeee e eeeee eeeeee ee eeeeeeee, eeeeeeeeeeee (88.8 ee, 8.8 eeee) eee eeeee eeeee eeeee. Mee eeee eee eeeeee eeee eee eeeee eeeee ee eee eeeeeeeee. Mee eeeeeeeee eee eeeeee eeeee eeeee eeee M8 eee eeee eeeeeeeeeee eeee M8 (88 eee). Mee eeeeeee eee eeeeeee eee 8 e ee 88 °M, eee eeee eee eeeeeeeee eee eeeeee ee ee eee eee eeeeeeeee M8 eee eeeeeeeee eeeeee. Mee eeeeeee eee eeeeeeee ee MM, eee eeee eeeeeee eeee Me8M (88 eM). 8 M MMe ee MeMM (8 eM) eee eeeee eee eee eeeeeeeeeee eeee eeeeeeeeeee eeeeee eee eeeeeeeee ee eeeeeeeeee eee eeeeee eeee Me8M eee MeMMe; eeeee: 88%.

References


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