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. Author manuscript; available in PMC: 2013 Sep 7.
Published in final edited form as: Org Lett. 2012 Aug 29;14(17):4458–4461. doi: 10.1021/ol301955s

Table 4.

Cross-Coupling of 4-Chloroanisole with Various Secondary Aminomethyltrifluoroborates 3a–g

graphic file with name nihms404418t56.jpg
entry R product yield (%)
1 n-Bu graphic file with name nihms404418t57.jpg 4d 97
2 i-Pr graphic file with name nihms404418t58.jpg 6a 83
3 graphic file with name nihms404418t59.jpg graphic file with name nihms404418t60.jpg 6b 69
4 graphic file with name nihms404418t61.jpg graphic file with name nihms404418t62.jpg 6c 81
5 Bn graphic file with name nihms404418t63.jpg 6d 90
6 graphic file with name nihms404418t64.jpg graphic file with name nihms404418t65.jpg 6e 73
7 graphic file with name nihms404418t66.jpg graphic file with name nihms404418t67.jpg 6f 85
a

Reaction conditions: 1.0 equiv of 4-chloroanisole 1.05 equiv of trifluoroborate, 4 mol % of XPhos-Pd-G2 A, 3 equiv of Cs2CO3, toluene/H2O = 4:1 (0.5 M), 85 °C, 3 h.