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. Author manuscript; available in PMC: 2011 Mar 24.
Published in final edited form as: J Am Chem Soc. 2010 Mar 24;132(11):3965–3972. doi: 10.1021/ja910900p

Table 4.

Alkylation of C-H Bondsa

graphic file with name nihms-181811-f0054.jpg
entry amide AlkI(Br) major product yield, %
1 graphic file with name nihms-181811-t0055.jpg i-Butyl iodide graphic file with name nihms-181811-t0056.jpg 58
2 graphic file with name nihms-181811-t0057.jpg n-Octyl iodide graphic file with name nihms-181811-t0058.jpg 47
3 graphic file with name nihms-181811-t0059.jpg n-Propyl iodide graphic file with name nihms-181811-t0060.jpg 77
4 graphic file with name nihms-181811-t0061.jpg graphic file with name nihms-181811-t0062.jpg graphic file with name nihms-181811-t0063.jpg 45
5 graphic file with name nihms-181811-t0064.jpg benzyl bromide graphic file with name nihms-181811-t0065.jpg 64
a

Amide (1 equiv), Pd(OAc)2 (0.05 equiv), base (2.5-3.5 equiv), pivalic acid (0.2 equiv), and RI or RBr (3-4 equiv) Yields are isolated yields. See the Supporting Information for details.