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oxidative addition with an aryl iodide that could
intramolecularly react through a six-membered transition
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9 The structure with 27.7 ppm in 31P NMR is not clear right
now. According to the literature, the 31P NMR signal of the
Au(III) intermediate is around 27 ppm (ref. 4b and 5).
¨
¨
3 For selected examples, see: (a) A. S. K. Hashmi, 10 A pyridine promoted diazonium decomposition through the
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11 Another possible mechanism is that the nucleophiles are
reacting with LAuCl to generate more electron-rich LAuNu,
which would be more susceptible to oxidation by
diazonium salts.
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S. Brase, Acc. Chem. Res., 2004, 37, 805; (b) A. Roglans,
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15 See recent example: A. Hubbard, T. Okazaki and K. K. Laali,
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16 (a) P. C. B. Page, R. D. Wilkes and D. Reynolds, in
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M. Majek and A. J. V. Wangelin, Chem. Commun., 2013, 49,
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6 The monitored quantitative rate constant kobs for sp2 C–C
coupling is (1.5 ꢂ 0.1) ꢃ 10ꢁ4 Sꢁ1 (ꢁ52 C), see ref. 3h; the
ꢀ
homo-coupling
product
was
generated
from
transmetallation between Au(III) and Au(I) intermediate
followed by reductive elimination, see ref. 3f.
7 R. Cai, M. Lu, E. Y. Aguilera, Y. Xi, N. G. Akhmedov,
J. L. Peterson, H. Chen and X. Shi, Angew. Chem., Int. Ed.,
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