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2.9.1.1.2 Reduction of Nitriles Using an In Situ Generated Ruthenium/Phosphine Catalytic System

DOI: 10.1055/sos-SD-227-00186

Bagal, D. B.; Bhanage, B. M.Science of Synthesis: Catalytic Reduction in Organic Synthesis, (20182377.

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.

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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]
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Me8M 88 8 88 [‌88‌]
Me eeee 888 8 88 [‌88‌]
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