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. Author manuscript; available in PMC: 2019 Nov 25.
Published in final edited form as: ACS Catal. 2018 Nov 29;9(1):216–223. doi: 10.1021/acscatal.8b04669

Table 1.

Optimization of Reaction Conditions to Promote Directed Alkyne Insertiona

graphic file with name nihms-1021585-t0009.jpg
entry T
(°C)
X
(equiv)
time
(h)
Y
(%)
yield of
3ab (%)
ratio of
3a/4ab
1c 115 2 2 10 51 1.1
2 115 2 1 10 76 5.5
3 80 2 1 10 81 7.2
4 60 2 2 10 79 8.8
5 60 1 2 10 67 9.3
6 45 2 24 10 74 10.5
7 45 1 24 10 74 10.3
a

A mixture of 0.1–0.2 mmol 1a, 0.1 mmol 2a, 0.225 mmol PhNNPh, 0.0025–0.01 mmol (THF)3TiI2(NPh), and 0.01 Ph3CH (internal standard) in 0.5 mL of CF3Ph were heated at desired temperature and time.

b

Yield and selectivity are determined by 1H NMR and reported with respect to 2a.

c

Reported in ref 8 with [py2TiCl2(NPh)]2 as catalyst.