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. 2017 Mar 8;8(5):3576–3585. doi: 10.1039/c7sc00138j

Table 3. Substrate scope in the hydrogenation of amides to alcohols and amines catalyzed by Mn-2 complex.

Inline graphic
Entry a Amide Mn-2 (mol%) Conv. b (%) Yield of amine b (%) Yield of alcohol b (%)
1 graphic file with name c7sc00138j-u4.jpg 2 >99 96 90
2 graphic file with name c7sc00138j-u5.jpg 2 94 88 85
3 graphic file with name c7sc00138j-u6.jpg 2 >99 90 n.d.
4 graphic file with name c7sc00138j-u7.jpg 2 90 84 80
5 graphic file with name c7sc00138j-u8.jpg 4 85 81 75
6 graphic file with name c7sc00138j-u9.jpg 4 >99 >99 >99
7 graphic file with name c7sc00138j-u10.jpg 3 94 85 80
8 c graphic file with name c7sc00138j-u11.jpg 3 >99 >99 90
9 graphic file with name c7sc00138j-u12.jpg 4 95 94 90
10 graphic file with name c7sc00138j-u13.jpg 4 85 82 80
11 graphic file with name c7sc00138j-u14.jpg 4 >99 98 94
12 graphic file with name c7sc00138j-u15.jpg 4 95 92 90
13 c graphic file with name c7sc00138j-u16.jpg 4 >99 >99 >99
14 d graphic file with name c7sc00138j-u17.jpg 2 95 90 85
15 c , d graphic file with name c7sc00138j-u18.jpg 2 82 81 78
16 d graphic file with name c7sc00138j-u19.jpg 3 >99 >99 >99
17 c , d graphic file with name c7sc00138j-u20.jpg 4 >99 >99 90
18 c , d graphic file with name c7sc00138j-u21.jpg 5 98 97 96

aStandard reaction conditions: amide (0.25 mmol), Mn-2 cat. (2–5 mol%), KOtBu (2.8 mg, 0.025 mmol, 10 mol%), cyclohexane (2 mL), 30 bar of H2, 100 °C over 16 h.

bConversion of the amide and yield of the alcohol and amine were calculated by GC using hexadecane as external standard.

cThe reaction was carried out using cyclohexane/t-amylOH (1.5/0.5) mixture as solvent (2 mL).

dRun at 120 °C.