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. Author manuscript; available in PMC: 2015 Sep 15.
Published in final edited form as: Angew Chem Int Ed Engl. 2014 Jul 24;53(38):10209–10212. doi: 10.1002/anie.201404579

Table 3.

Reaction Scope with Respect to Alkynes [a]

graphic file with name nihms626761t12.jpg

Entry R1, R2 Product Yield, %
1 CH2OH
CH2OH
graphic file with name nihms626761t13.jpg 95
2 Me
Me
graphic file with name nihms626761t14.jpg 96
3 H
Ph
graphic file with name nihms626761t15.jpg 95
4 H
tBu
graphic file with name nihms626761t16.jpg 73
5[b] Ph
Me
graphic file with name nihms626761t17.jpg 95
6[c] CO2Et
H
graphic file with name nihms626761t18.jpg 82
7 TIPS
H
graphic file with name nihms626761t19.jpg 64
8[d] cyclopropyl
H
graphic file with name nihms626761t20.jpg 84
9[e] CH2 NPhth
H
graphic file with name nihms626761t21.jpg 93
[a]

Amide 0.5 mmol, CF3CH2OH 5 mL, alkyne 1.2 equiv, air. Yields are isolated yields. Please see Supporting information for details.

[b]

Isolated as 14/1 isomer mixture.

[c]

Minor isomer (13%) also isolated.

[d]

Isolated as 13/1 isomer mixture.

[e]

Isolated as 7/1 isomer mixture, reaction time: 18 h.