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. Author manuscript; available in PMC: 2014 Jun 17.
Published in final edited form as: Angew Chem Int Ed Engl. 2013 May 2;52(25):6508–6512. doi: 10.1002/anie.201301601

Table 1.

Optimization of the Reaction Conditions a

graphic file with name nihms488994t1.jpg
entry 1a/2a catalyst yieldb
1 1:1.2 LAuCl (5 mol %)/NaBArF4 (10 mol %) <7 c
2 1:1.2 Me-DalPhosAuCl (5 mol %)/NaBArF4(10 mol %) 11%
3 1:1.2 Mor-DalPhosAuCl (5 mol %)/NaBArF4(10 mol %) 68%
4 1:1.2 L1AuCl(5 mol %)/NaBArF4(10 mol %) 68%
5 1:1.2 L2AuCl(5 mol %)/NaBArF4(10 mol %) 68%
6 1:1.2 L3AuCl(5 mol %)/NaBArF4(10 mol %) 18%
7 1:1.2 L4AuCl(5 mol %)/NaBArF4(10 mol %) 75%
8 1:1.2 L5AuCl(5 mol %)/NaBArF4(10 mol %) 84%
9 1:1.2 L6AuCl(5 mol %)/NaBArF4(10 mol %) 30%
10 1:1.2 L7AuCl(5 mol %)/NaBArF4(10 mol %) 79%
11 1:1.2 L8AuCl(5 mol %)/NaBArF4(10 mol %) 63%
12 1.3/1 L7AuCl(5 mol %)/NaBArF4(10 mol %) 86%
13 1.3/1 L5AuCl(5 mol %)/NaBArF4(10 mol %) 98% d
14 1.3/1 L5AuCl(5 mol %)/NaBArF4(10 mol %)e 95%
15 1.3/1 L5AuCl(5 mol %)/NaBArF4(10 mol %)f 88%
a

The reaction was run with everything except the oxidant in a vial capped with a septum, and the oxidant was introduced into the reaction mixture in 12 h using a syringe pump. Initially, [1a] = 0.1 M.

b

Measured by 1H NMR analysis using diethyl phthalate as the internal standard.

c

L = Ph3P, IPr, or BrettPhos; the crude 1H NMR spectra were mostly messy.

d

96% isolated yield.

e

DCE was used as the solvent.

f

toluene was used as the solvent.