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. Author manuscript; available in PMC: 2011 Aug 25.
Published in final edited form as: J Am Chem Soc. 2010 Aug 25;132(33):11768–11778. doi: 10.1021/ja1047363

Table 2.

Survey of the fluoride sources for the macrocyclizationa

graphic file with name nihms-225748-f0008.jpg
entry fluoride source solvent equiv yield, % 8a+8a' ratiob8a+8a'
1 TMAF•4H2O DMF 5 47 100:0
2 TMAF•6H2O DMF 5 34 100:0
3 BTMAF DMF 5 39 2:1
4 BTMAF•6H2O DMF 5 49 6:1
5 BTMAF•10H2O DMF 5 0 -
6 TEAF•2H2O DMF 5 32 2:1
7 TEAF•6H2O DMF 5 40 2:1
8 TBAT THF 5 29 100:0
9 TASF THF 5 22 100:0
10 CsF DMF 5 0 -
a

Reaction conditions employed 0.25 mmol of 7 at 0.1 M.

b

Ratio determined by 1H NMR.