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. 2018 Jan 24;3(1):863–871. doi: 10.1021/acsomega.7b01688

Table 6. Effect of the Catalyst Loading on the Reaction Efficiency [Yields, Isomeric Content (α/β Ratio) and TONs]a,b.

    yields, isomeric ratio, and TON under selected conditions
entry catalyst loading, mol % 80 °C/6 h 100 °C/4 h
1–2 1 83 (17/83) 83 82 (17/83) 82
3–4 0.1 90 (19/81) 900 85 (48/52) 850
5–6 0.01 85 (68/32) 8500 77 (68/32) 7700
7–8 0.001 9 (64/36) 9000 7 (62/38) 7000
9–10 0.0001 <5 <5
a

PhC≡CH (5.0 × 10–4 mol, 1 equiv), Et3SiH (5.0 × 10–4 mol, 1 equiv), catalyst 18; toluene (0.5 mL).

b

Yields of products were determined by 1H NMR spectroscopy using 1,2-dimethoxyethane as the standard, whereas the isomeric content was determined on the basis of the alkene coupling constants.