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. Author manuscript; available in PMC: 2022 Feb 25.
Published in final edited form as: J Med Chem. 2020 Nov 17;63(23):14951–14978. doi: 10.1021/acs.jmedchem.0c01464

Table 1.

Optimization of Allene Formation with Stryker’s Reagent ([CuHPPh3]6).

graphic file with name nihms-1776635-t0012.jpg
Entry SM Equiv Stryker’s Temp (°C) Time (h) Total yield (%) (24a/25a):(31a/32a):SM Scale (mg)
1 23a 1.8 0 1.5 64 100:trace:0 110a
2 23a 1 0 1 73 60:40:0 110
3 23a 0.8 −10 2 66 63:25:12 110
4 23a 0.9 −20 2 58 80:20:0 110
5 23a 0.9 −10 2 78 77:23:0 220
6 23a 0.9 −10 2 49 72:19:9 440
7 22a 0.9 −10 2 70 70:16:0b 110
8 22a 0.9 −10 1.5 56 90:10:0 122

SM = starting material

a

Reaction performed with a previously-opened aged container of Stryker’s reagent; all other reactions were performed with the newly opened container

b

14% of the total yield was a product resulting from reduction of the alkyne.