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. Author manuscript; available in PMC: 2010 May 15.
Published in final edited form as: J Org Chem. 2009 May 15;74(10):3689. doi: 10.1021/jo802784w

TABLE 4.

Condensation Reactions of Fluoro Julia Reagents 16 and 17

graphic file with name nihms109915t18.jpg
rxn substrate sulfone: molar equiv;a DBU: molar equiva rxn time, T Products 18–23, yieldb
1 graphic file with name nihms109915t19.jpg 16: 3; DBU: 4 0.5 h, reflux R = Ph: 18a, 61%
2 17: 3 ; DBU: 6 16 h, 0–5 °C R = n-Pr. 18b, 89%
3 graphic file with name nihms109915t20.jpg 16: 4; DBU: 6 0.5 h, reflux R = Ph: 19a, 64%
4 graphic file with name nihms109915t21.jpg 16: 2; DBU: 4 0.5 h, reflux R = Ph:20a, 81%
5 17: 2; DBU: 6 8 h, 0 °C - rt R = n-Pr: 20b, 86%
6 graphic file with name nihms109915t22.jpg 16: 4; DBU: 3 40 min, reflux R = Ph:21a, 71%
7 graphic file with name nihms109915t23.jpg 17: 3; DBU: 6 8 h, 0–5 °C R = n-Pr: 22b, 90%
8 graphic file with name nihms109915t24.jpg 17: 1.5; DBU: 6 3 h, 0–5 °C R = n-Pr: 23b, 73%
a

Total amount of sulfone and DBU used for complete aldehyde consumption. For good conversions, sequential addition of sulfone and DBU was required (please see the Experimental Section and the Supporting Information for details).

b

Yields of isolated, purified products.