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. Author manuscript; available in PMC: 2014 Dec 20.
Published in final edited form as: J Org Chem. 2013 Nov 19;78(24):10.1021/jo4023233. doi: 10.1021/jo4023233

Table 2.

Scope of the Trifluoromethylation of Alkynyl- and Alkenyltrifluoroborates

graphic file with name nihms542612u2.jpg
Entry Substrate Method a Product Yield b
1 graphic file with name nihms542612t23.jpg
3a
A graphic file with name nihms542612t24.jpg
5a
50% (−)
2 graphic file with name nihms542612t25.jpg
3b
A graphic file with name nihms542612t26.jpg
5b
51% (45%)
3 graphic file with name nihms542612t27.jpg
4a
A graphic file with name nihms542612t28.jpg
6a
54% (−)c
4 graphic file with name nihms542612t29.jpg
4b
A graphic file with name nihms542612t30.jpg
6b
77% (77%)c
5 graphic file with name nihms542612t31.jpg
4c
A graphic file with name nihms542612t32.jpg
6c
70% (59%)
6 graphic file with name nihms542612t33.jpg
4d
A graphic file with name nihms542612t34.jpg
6d
12% (10%)
7 graphic file with name nihms542612t35.jpg
4e
A - -
a

Conditions A: NaSO2CF3 (3.0 equiv), TBHP (5.0 equiv), CuCl (1.0 equiv), CH2Cl2/MeOH/H2O, 1:1:0.8 ([3 or 4] = 0.1 M), open flask, rt, 12 h.

b

Yields determined by 19F analysis; isolated yields are reported in brackets.

c

With ~5% of the (Z) product.