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. Author manuscript; available in PMC: 2013 Dec 14.
Published in final edited form as: Adv Synth Catal. 2012 Dec 4;354(18):3517–3522. doi: 10.1002/adsc.201200738

Table 5.

Comparison of Pd/Ir-catalyzed C–H phenylation with Ph2I+ vs Pd/Rucatalyzed C–H phenylation with PhN2+.

Substrate Product Yield (%) with Ph2I +[a,b] Yield (%)with PhN2+[a,c]
graphic file with name nihms491460t23.jpg
(1) 		1a 89 91
graphic file with name nihms491460t24.jpg
(3) 		3a 69[d] 89
graphic file with name nihms491460t25.jpg
(5) 		5a 54 25
graphic file with name nihms491460t26.jpg
(6) 		6a 52 38
graphic file with name nihms491460t27.jpg
(7) 		7a 11 8
graphic file with name nihms491460t28.jpg
(10) 		10a 52 23
graphic file with name nihms491460t29.jpg
(11) 		11a 63 68
graphic file with name nihms491460t30.jpg
(17) 		graphic file with name nihms491460t31.jpg <1[e] 66
[a]

GC calibrated yield.

[b]

General conditions: substrate (1 equiv), [Ph2I]OTf (2 equiv), Pd(NO3)2 (0.10 equiv), Ir(ppy)2(dtbbpy)PF6 (0.05 equiv), MeOH (0.2 M in substrate), 26 W lightbulb, 15 h, r.t., degassed by sparging with N2.

[c]

General conditions: substrate (1 equiv), [PhN2]BF4 (4 equiv), Pd(OAc)2 (0.10 equiv), Ru(bpy)3Cl2•6H2O (0.025 equiv), MeOH (0.1 M in substrate), 26 W lightbulb, r.t., 15 h, degassed by sparging with N2.

[d]

[Ph2I]BF4 was the oxidant.

[e]

Product 17a was not detected by GC, and only traces amounts of 17 and 3′-methylacetophenone were formed.