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. Author manuscript; available in PMC: 2020 May 6.
Published in final edited form as: Inorg Chem. 2019 Jun 12;58(16):10508–10515. doi: 10.1021/acs.inorgchem.9b01082

Table 1.

Screening of Reaction Conditionsa

graphic file with name nihms-1582301-t0009.jpg
entry CpR2Mb catalyst % yield 2c % yield 3d
1 Cp2Ti TiI4(THF)2e >95 0
2 Cp2Ti TiI4(THF)2 0 >95
3 Cp*2Ti TiI4(THF)2 0 0
4 Cp*2Zr TiI4(THF)2 71 0
5 Cp*2Zr TiI4(THF)2f 55 0
6 Cp*2Zr TiBr4(THF)2 trace 0
7 Cp*2Zr TiCl4(THF)2 trace 0
8 Cp*2Zr TiI4(THF)2g 0 0
9 Cp*2Zr none 0 0
a

Reaction conditions: metallocene (0.05 mmol), diphenylacetylene (0.05 mmol), catalyst (0.05–0.0005 mmol of Ti), Zn0 (0.05–0.0005 mmol), 0.5 mL of C6H5Br, 115 °C, 3 h.

b

Cp = cyclopentadiene; Cp* = pentamethylcyclopentadiene.

c

Determined by quantitative GC-FID with respect to an internal standard (1,3,5-trimethoxybenzene).

d

Determined by 1H NMR with respect to an internal standard (1,3,5-trimethoxybenzene).

e

Reaction conducted with 100 mol % TiI4(THF)2.

f

Reaction conducted with 0.1 mmol of diphenylacetylene.

g

Reaction conducted in the absence of Zn0.