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. Author manuscript; available in PMC: 2014 Jun 5.
Published in final edited form as: J Am Chem Soc. 2013 May 24;135(22):8213–8221. doi: 10.1021/ja403165u

Table 1.

Ligand and Additive Effects on Pd-Catalyzed Dehydrogenation of 3-Methylcyclohexanone, 1a, and 3-Methylcyclohexenone, 1b.

graphic file with name nihms481941u1.jpg
Entry Additive Substrate: 1a 1b
Yield of 2 (%)a
1 none 28 52
2 graphic file with name nihms481941t1.jpg 16 39
3 graphic file with name nihms481941t2.jpg 44 59
4 graphic file with name nihms481941t3.jpg /TsOH (0%) 24 53
5 /TsOH (12%) 79 74
6 graphic file with name nihms481941t4.jpg /TsOH (0%) 45 98
7 /TsOH (6%) 48 95
8 /TsOH (12%) 50 81
9 graphic file with name nihms481941t5.jpg /TsOH (0%) 45 78
10 /TsOH (6%) 50 90
11 /TsOH (12%) 57 86
12 Pd/C instead of Pd(TFA)2 1 < 2
13 Pd/Al2O3 instead of Pd(TFA)2 0 < 1
a

Entries 1–5, 12, and 13 obtained from reference 3a.