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. Author manuscript; available in PMC: 2017 Mar 30.
Published in final edited form as: J Am Chem Soc. 2016 Mar 18;138(12):4260–4266. doi: 10.1021/jacs.6b01578

Table 1.

Optimization of Pd-Catalyzed C-3 and Benzylic Arylation of 1aa

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entry base 3ab (%)a 4ab (%)a 5ab (%)a
1 KN(SiMe3)2 93(93)b 6 0
2 NaN(SiMe3)2 <5 <5 29
3 LiN(SiMe3)2 0 0 0
4 KN(SiMe3)2:18-crown-6c 0 13 51
5 NaN(SiMe3)2:l5-crown-5c 0 <5 39
6 LiN(SiMe3)2:12-crown-4c 0 0 94(91)b
a

Yield determined by 1H NMR spectroscopy of the crude reaction mixture.

b

Isolated yield after chromatographic purification.

c

Crown ether (2 equiv relative to base) employed.