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. Author manuscript; available in PMC: 2014 Nov 20.
Published in final edited form as: J Am Chem Soc. 2013 Nov 12;135(46):17602–17609. doi: 10.1021/ja409511n

Table 3.

Scope of Heterocyclic Diarylmethanes in the Allylic Substitutiona

graphic file with name nihms536713t15.jpg
Entry Pronucleophlles Base Products Yieldb (%)
1c graphic file with name nihms536713t16.jpg 1a NaN(SiMe3)2 graphic file with name nihms536713t17.jpg 3aa 99
2c graphic file with name nihms536713t18.jpg 1b LiN(SiMe3)2 graphic file with name nihms536713t19.jpg 3ba 99
3 graphic file with name nihms536713t20.jpg 1c KN(SiMe3)2 graphic file with name nihms536713t21.jpg 3ca 91
4 graphic file with name nihms536713t22.jpg 1d NaN(SiMe3)2 graphic file with name nihms536713t23.jpg 3da 82
5d graphic file with name nihms536713t24.jpg 1e NaN(SiMe3)2 graphic file with name nihms536713t25.jpg 3ea 80
6 graphic file with name nihms536713t26.jpg 1f NaN(SiMe3)2 graphic file with name nihms536713t27.jpg 3fa 93
7 graphic file with name nihms536713t28.jpg 1g LiN(SiMe3)2 graphic file with name nihms536713t29.jpg 3ga 85
a

Reaction conducted on a 0.1 mmol scale with 1 equiv of 1 and 2 equiv of 2a at 0.1 M .

b

Isolated yield after chromatographic purification.

c

1 mol % Pd(COD)Cl2, 1.5 mol % Xantphos.

d

2.5 equiv of NaN(SiMe3)2 and 2.5 equiv of 15-crown-5.