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. Author manuscript; available in PMC: 2015 Aug 28.
Published in final edited form as: Org Biomol Chem. 2014 Jul 3;12(32):6190–6199. doi: 10.1039/c4ob01088d

Table 1.

Optimization of the reaction conditions.a

graphic file with name nihms611330u1.jpg
Entry Base/fluoride (equiv) Solvent T (°C) 2 : 3 : quinolineRatiob Yieldb of 3, %
1 TBAF (0.2) THF 23 7 : 1 : 1 11
2 TBAF (0.2) PhCH3/THF (1:1) 23 1.7 : 1.5 : 1 34
3 TBAF (0.2) PhCH3/THF (1:1) 65 10 : 1 : 1.5 8
4 TASF (1.1) PhCH3/THF (1:1) 23 2 : 2.5 : 1 44
5 CsF (1.1) PhCH3/THF (1:1) 23 1.6 : 1.7 : 1 34
6c TASF (1.1) PhCH3/THF (1:1) 23 1.3 : 2.5 : 1 50
7d TASF (1.1) THF 23 1.5 : 2.1 : 1 44
8 KOt-Bu (1.1) THF 23 1 : 6.8 : 17.3 26
9 KOt-Bu (3) THF 23 1 : 3.2 : 5.8 32
10e KOt-Bu (3) THF −20 1 : 29 : 3.2 87
a

Reaction conditions: 2 (0.35 or 1 mmol), 1 (2.5 equiv), in the solvent (c=0.7 M) under Ar for 2 h.

b

Determined by 1H NMR.

c

(CuOTf)2·PhH (5 mol %) was added.

d

MgCl2 (2 equiv) was added.

e

c=0.2 M.