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. 2021 Dec 22;27(1):33. doi: 10.3390/molecules27010033

Table 1.

Optimization of SOMOphilic alkynylation of alkenes a.

graphic file with name molecules-27-00033-i001.jpg

Entry Variation from the “Standard Conditions” Yield (%) b
Entry 1 none 85 (81) c
Entry 2 2a′ instead of 2a 80 (72) c
Entry 3 2a″ instead of 2a 71
Entry 4 2a‴ instead of 2a 49
Entry 5 2a⁗ instead of 2a ND
Entry 6 2a′′′′′ instead of 2a ND
Entry 7 Only EtOH instead of EtOH and (CH2OH)2 62
Entry 8 Fe(acac)3 (20 mol%) instead of Fe(acac)3 (30 mol%) 60
Entry 9 In(acac)3 instead of Fe(acac)3 ND
Entry 10 Co(acac)3 instead of Fe(acac)3 ND
Entry 11 FeCl3 instead of Fe(acac)3 45
Entry 12 1a (0.2 mmol), 2a (0.3 mmol) 65

a Standard conditions: 1a (0.3 mmol, 1.5 equiv), 2a (0.2 mmol, 1.0 equiv), Fe(acac)3 (30 mol%), PhSiH3 (0.4 mmol, 2.0 equiv), in EtOH (0.8 mL) and (CH2OH)2 (0.2 mL) at 35 °C for 12 h. b Determined by GC-MS using dodecane as the internal standard. c Isolated yield in parentheses.