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. Author manuscript; available in PMC: 2022 Jun 18.
Published in final edited form as: Tetrahedron. 2021 May 11;90:132173. doi: 10.1016/j.tet.2021.132173

Table 14.

Survey of pyridine ligands for C–H methylationa.

graphic file with name nihms-1703004-t0019.jpg
Entry Ligand Yield %(7/4e)
1 L2 7/70
2 L10 14/70
3 L11 14/71
4 L12 10/71
5 L13 0/100
6 L14 0/95
7 L15 8/92
8 L16 6/94
9 b L2 + L10 19/67

graphic file with name nihms-1703004-f0020.jpg

a

Standard conditions are 4e (0.2 mmol, 1.0 equiv), Mel (3.0 equiv), Pd(OAc)2 (10 mol %), ligand (20 mol %), N9 (30 mol %), AgOAc (3.0 equiv), CHCl3 (1.0 mL, 0.2 M), under air, 100 °C, 24 hours.

b

20 mol % of L10 and 10 mol % L2 added.