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. Author manuscript; available in PMC: 2018 Jun 14.
Published in final edited form as: J Am Chem Soc. 2017 Jun 5;139(23):7721–7724. doi: 10.1021/jacs.7b04024

Table 2.

Evaluation of Pyridine Derivatives as Additives

graphic file with name nihms904613u3.jpg
entry additive/equiv Pd catalyst 7:8:9a yield of 9 (%)a
1 pyridine/1.0b Pd-QPhos-G3 6:1:1 5
2 DMAP/1.0b Pd-QPhos-G3 1:1:4 17
3 DMAP/1.0 Pd-QPhos-G3 2:1:3 34
4 DMAP/1.0 Pd-Pt-Bu3-G3 4:1:2 14
5 DMAP/1.0 Pd-APhos-G3 1:1:5 27
6 DMAP/1.0 Pd-Pt-Bu2CH2t-Bu-G3 1:1:11 68
7 DMAP/1.0c Pd-Pt-Bu2CH2t-Bu-G3 2:1:13 67
8 DMAP/2.0c Pd-Pt-Bu2CH2t-Bu-G3 1:1:>20 61
9 DMAP/2.0c [Pd-G3]2 n.d. <2
10 DMAP/2.0c,d Pd-Pt-Bu2CH2t-Bu-G3 n.d. <2
a

Yield and (1,2):(1,4) determined by 1H NMR analysis using 1,3,5-trimethoxybenzene as an internal standard.

b

Reaction run with 1.5 equiv of (Bpin)2 and 2.0 equiv of KOt-Bu.

c

Reaction run at 45 °C instead of 22 °C.

d

Reaction run with 5 mol% CuBr instead of 5 mol% It-BuCuBr. n.d. = not determined