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. Author manuscript; available in PMC: 2010 Feb 7.
Published in final edited form as: J Org Chem. 2009 Feb 6;74(3):1141–1147. doi: 10.1021/jo802196r

Table 1.

Preparation of the Requisite Terminal Alkynes a

graphic file with name nihms86669t1.jpg
entry XR1 Coupling
conditionsb 		TMS-alkyne
(% yield)		 Deprotection
conditionsc 		Terminal alkyne
(% overall yield)
1 SMe A 1 (97) aq KOH/MeOH 0.5 h/25 °C 5 (83)
2 CO2Me A 2 (100) KF-2H2O/MeOH 36 h/25 °C 6 (82)
3 Ph A -d - -
4 CONHPh B 3 (80) KF-2H2O/MeOH 0.5 h/25 °C 7 (71)
5 NMe2 C 4 (74) Aq NaOH/MeOH/ether 0.16 h/25 °C 8 (48)
a

All reactions have been run with 5 mmol of o-iodoarene.

b

Reaction conditions: (A) 1.2 equiv of alkyne, 2 mol % PdCl2(PPh3)2, 1 mol % CuI, 20 mL of Et3N, 25 °C. (B) 1.3 equiv of alkyne, 3 mol % PdCl2(PPh3)2, 2 mol % CuI, 4 equiv of DIPA, DMF, 65 °C. (C) 1.2 equiv. of alkyne, 1 mol % PdCl2(PPh3)2, 3 mol % CuI, 0.9 equiv of Et3N, DMF, 25 °C.

c

See the Supporting Information for the experimental details.

d

A complex reaction mixture was obtained.