22
J. Oliver–Meseguer and A. Leyva–Pérez
O
O
O
O
O
O
Cl
O
O
O
O
O
O
4
(82 % at 50 ppm)
(64% conversion at 1 ppm)
a
5
(53 % at 5 ppm)
10
(74 % at 100 ppm)
6
(91 % at 1 ppm)
(64 % at 10 ppb)
O
O
O
9
(69 % at 100 ppm)
O
O
O
O
OMe
7
(78 % at 200 ppm)
O
O
O
11
(64 % at 100 ppm)
O
O
O
O
8
13
(99 % at 50 ppm)
O
O
O
8
(88 % at 10 ppb)
O
O
O
12
(60 % at 50 ppm)
O
O
Fig. 1.20 a Ester-assisted hydration of in situ formed alkyne reaction. b Plot time conversion for
AuCl (squares) and HAuCl 4 (diamonds) at 100 ppm, after correction with the blank experiment. c
Turnover number (TON) and turnover frequency (TOF) for different amounts of AuCl, calculated
as moles of 4 formed per mole of AuCl at final conversion (TON) and as the initial reaction rate after
the induction time per mole of AuCl (TOF). The final yield of 4 is > 90% in all cases, except for
0.01 ppm, where it is ~ 50%. d Absorption measurements (a.u., arbitrary units) for the hydration of
3 containing the Au active species along the induction time (a) and when the reaction proceeds (b)
with the corresponding fluorescence (inset, irradiated at 349 nm). Bottom, reaction scope (isolated
yields and ppm of Au in parentheses (Fig. from Ref. [49]. Copyright © 2012 by AAAS)