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. Author manuscript; available in PMC: 2019 Oct 10.
Published in final edited form as: J Am Chem Soc. 2018 Oct 2;140(40):12829–12835. doi: 10.1021/jacs.8b05870

Table 1.

Initial Investigation of the Synthesis of (Z)-2-Iodovinyl Phenyl Ethera

graphic file with name nihms-1023529-t0007.jpg
entry t (h) equiv 1b solvent base yield (%)
1 14 1.5 DMSO Cs2CO3 47 (46†)
2 14 1.5 DMAc Cs2CO3 44
3 14 1.5 DMF Cs2CO3 47
4 14 1.5 CH3CN Cs2CO3 75 (74b)
5 14 1.0 CH3CN Cs2CO3 46
6 14 2.0 CH3CN Cs2CO3 61
7 14 3.0 CH3CN Cs2CO3 51
8 2 1.5 CH3CN Cs2CO3 35
9 4 1.5 CH3CN Cs2CO3 48
10 14 1.5 CH3CN Cs2CO3 24c
11 14 1.5 CH3CN DBU 20
12 14 1.5 CH3CN MTBD 40
13 14 1.5 CH3CN TBD 79 (78b)
14 14 1.5 CH3CN TMG trace
15 14 1.5 DMSO TBD 53
16 14 1.5 THF TBD 37
17 14 1.5 THF TMG 20
a

Reaction conditions: 1b (0.30 mmol), 2a (0.20 mmol), base (0.30 mmol), solvent (1.5 mL), room temperature, N2. Yields are determined by 1H NMR using 1,3,5-trimethoxybenzene as an internal standard.

b

Isolated yield.

c

Reaction carried out under air. t: time; DBU: 1,8-diazabicyclo[5.4.0]undec-7-ene; MTBD: 7-methyl-1,5,7-triazabicyclo[4.4.0]dec-5-ene; TBD: 1,5,7-triazabicyclo[4.4.0]dec-5-ene; TMG: 1,1,3,3-tetramethylguanidine; DMAc: N,N′-dimethylace-tamide; DMF: N,N′-dimethylformamide; DMSO: dimethyl sulfoxide; THF: tetrahydrofuran.