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Table 1 The effect of different parameters on the reaction of 1a and 2a.a

From: Cu-catalyzed, Mn-mediated propargylation and allenylation of aldehydes with propargyl bromides

Entry [Cu] Solvent Mn Time/h Yield/% of 3ab
1 CuBr2 MeCN 12 Trace
2 MeCN Mn 12 16
3 CuBr2 MeCN Mn 12 47
4 CuBr2 THF Mn 12 Trace
5 CuBr2 DCM Mn 12 Trace
6 CuBr2 EtOH Mn 12 24
7c CuBr2 MeCN Mn 12 24
8d CuBr2 MeCN Mn 12 13
9 CuSO4 MeCN Mn 12 59
10 CuCl MeCN Mn 12 83
11 CuCl2 MeCN Mn 12 63
12 CuBr MeCN Mn 12 74
13 CuI MeCN Mn 12 41
14e CuCl MeCN Mn 12 75
15f CuCl MeCN Mn 12 33
16 CuCl MeCN Mn 24  > 99
  1. aReaction conditions: All reactions were performed with 1a (0.5 mmol), 2a (1.5 equiv.), copper catalyst (10 mol%), Mn powder (3 equiv.), CF3COOH (25 mol%), solvent (2 mL), at room temperature under N2 atmosphere. b Yield was determined by GC with dodecane as internal standard based on 1a. c Reaction in the air. d Without CF3COOH. e 5.0 equiv. of Mn was added. f CuCl (20 mol%) was added.