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. Author manuscript; available in PMC: 2019 Feb 7.
Published in final edited form as: J Am Chem Soc. 2018 Jan 29;140(5):1627–1631. doi: 10.1021/jacs.8b00643

Table 2.

Yield Comparison with Alternative Methods of Nitrile Dehydrationa

Method graphic file with name nihms936565t1.jpg graphic file with name nihms936565t2.jpg graphic file with name nihms936565t3.jpg graphic file with name nihms936565t4.jpg
2% [Cu], DMMS, rt 97% 85% 80% 93%
5% [Fe], DEMS, 100 °C6g 85% 23% 75% 49%
5% [Fe], DEMS, rt <5% <5% 24% <5%
POCl3, Et3N, rt 98% 27% 38% 42%
T3P, 100 °C 86% 48% 13% 68%
5% TBAF, PhSiH3, 100 °C6p 87% 8% 62% 47%
5% TBAF, PhSiH3, rt 7% <5% 16% 5%
a

Yields were assessed by GC analysis of the crude reaction mixture, using dodecane as an internal standard. See supporting information for reaction conditions and details.