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. Author manuscript; available in PMC: 2021 Jun 3.
Published in final edited form as: J Am Chem Soc. 2020 May 19;142(22):9932–9937. doi: 10.1021/jacs.0c03993

Table 1.

Optimization of Reaction Conditionsa

graphic file with name nihms-1615816-t0001.jpg
Entry Deviation from standard conditions 4:5:6:7b Yield of 4ac
1 None 98:1:0.5:0.5 89% (80%)
2 (E)/(Z)-1 (1:1.2) 96:1:1:2 83% (75%)
3 45 or 80 °C (dark) 8:0:0:92 Trace
4 Without PdCl2 4:0:0:96 Trace
5 Without AgNTf2 91:5:2:2 48%d
6 Without Cs2CO3 62:29:7:2 44%
a

0.2 mmol scale; (E)-1:2:3 = 1:1.3:1.3.

b

Determined by GC/MS using pentadecane as internal standard; 4a:4b > 20:1.

c

Determined by 1H NMR using dibromomethane as internal standard; isolated yields given in parentheses.

d

Formation of substantial amounts of radical dimerization products was observed.