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. Author manuscript; available in PMC: 2008 Sep 15.
Published in final edited form as: J Am Chem Soc. 2006 Nov 29;128(47):15050–15051. doi: 10.1021/ja0647708

Table 2.

Iron-catalyzed carbomagnesiation of propargylic and homopropargylic alcohols.a

graphic file with name nihms63700f4.jpg
entry Conditions Product Yield (%)b
1 Fe(ehx)3 (0.20 equiv) dppe (0.20 equiv) graphic file with name nihms63700t1.jpg
R = n-C10H21 		75
2 Fe(ehx)3 (0.20 equiv) dppe (0.20 equiv) R = TBSO(CH2)4 80
3 Fe(ehx)3 (0.20 equiv) dppe (0.20 equiv) R = BnO(CH2)3 70
4 Fe(acac)3 (0.20 equiv) dppe (0.20 equiv) graphic file with name nihms63700t2.jpg 78
5 Fe(acac)3 (0.30 equiv) dppe (0.30 equiv) graphic file with name nihms63700t3.jpg 85
6 Fe(acac)3 (0.15 equiv) graphic file with name nihms63700t4.jpg 81
7 Fe(acac)3 (0.30 equiv) graphic file with name nihms63700t5.jpg
99% ee		 61
8 Fe(ehx)3 (0.30 equiv) dppe (0.30 equiv) graphic file with name nihms63700t6.jpg 80
9c Fe(acac)3 (0.20 equiv) graphic file with name nihms63700t7.jpg 75
10c Fe(acac)3 (0.20 equiv) graphic file with name nihms63700t8.jpg 74
11 Fe(acac)3 (0.50 equiv) CuBr (0.60 equiv) graphic file with name nihms63700t9.jpg 69
12c Fe(acac)3 (0.40 equiv) graphic file with name nihms63700t10.jpg 63
13d Fe(acac)3 (0.20 equiv) NMP (2.0 equiv) graphic file with name nihms63700t11.jpg
R=n-C10H21 		70
14d Fe(acac)3 (0.20 equiv) NMP (2.0 equiv) R= TBSO(CH2)4 74
a

Reactions carried out in THF (0.1M in substrate) using 5.0 equivalents of RMgBr at 0 °C for 7h unless otherwise indicated.

b

Isolated yield.

c

In toluene at 23 °C.

d

NMP = N-methyl pyrrolidine.