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. Author manuscript; available in PMC: 2016 Oct 12.
Published in final edited form as: Aldrichimica Acta. 2011;44(3):55–62.

Table 3.

Oxidation of styrenyl substrates with the Pd(NHC)–TBHP system.59

graphic file with name nihms818139u3.jpg
Ar R′ time (h) % conversion % yield H:I
Ph H 24 >99 75 >130:1
2-MePh H 48 >99 79 36:1
3-MePh H 32 >99 83 22:1
4-MePh H 16 >99 86 22:1
2,4,6-MePh H 24 95 71 >150:1
3-CIPh H 48 >98 80 >150:1
3-NO2Pha H 24 90 79 >150:1
Phb Ph 48 NA 42c 42:35
Ph Me 48 97 NA 2.3:1d
a

Conditions: 2.25 mol % [Pd(IiPr)Cl2]2, 12 mol % AgOTf.

b

Conditions: [alkene] = 0.3 M, 1.25 mol % [Pd(IiPr)Cl2]2, 4 mol % AgOTf, 35–50 °C.

c

Two equivalents of benzaldehyde produced via oxidative cleavage.

d

H is a 53:47 mixture of regioisomeric ketones.