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. Author manuscript; available in PMC: 2019 Aug 15.
Published in final edited form as: J Am Chem Soc. 2018 Jul 31;140(32):10233–10241. doi: 10.1021/jacs.8b05113

Table 3.

Change in Z Selectivity Over Time

graphic file with name nihms-1043136-t0015.jpg
Ar 20 min 25 min 30 min 35 min 40 min Yield d
graphic file with name nihms-1043136-t0016.jpg 20:1 18:1 13:1 10:1 10:1 92 – 95
graphic file with name nihms-1043136-t0017.jpg >100:1c 18:1 18:1 17:1 13:1 70 – 79
graphic file with name nihms-1043136-t0018.jpg 28:1 28:1 27:1 26:1 25:1 84 – 89
a

Reported selectivities of crude reaction mixture.

b

i-BuOH used instead of MeOH

c

Reaction mixture contains <10% of alkyne.

d

Combined yileds of Z and E isomers.