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. Author manuscript; available in PMC: 2022 Apr 2.
Published in final edited form as: Org Lett. 2021 Mar 19;23(7):2836–2840. doi: 10.1021/acs.orglett.1c00851

Table 1.

Reaction Condition Deoptimization

graphic file with name nihms-1686691-t0002.jpg
Entrya Variation from the standard conditions Yield 4ab
1 None 97%c
2 No [Cp*Rh(MeCN)3](SbF6)2 0%
3 [Cp*RhCl2]2 (5%) / AgSbF6 (20%) 91%
4 [Cp*IrCl2]2 (5%) / AgSbF6 (20%) 0%
5 [Cp*Co(CO)I2] (10%) / AgSbF6 (20%) 0%
6 [RuCl2(p-cymene)]2 (5%) / AgSbF6 (20%) 0%
7 No NaOAc 87%
8 Cp*Rh(OAc)2 (10%)d 0%
9 Cp*Rh(OAc)2 (10%) / AgSbF6 (20%)d 86%
10 DCE as solvent 77%
11 0.5 M 91%
12 50 °C 85%
13 2:3:1 ratio 1a:2a:3a 63%
a

Conditions: 0.10 mmol of 1a, 0.30 mmol of 2a, 0.20 mmol of 3a

b

Yields determined by 1H NMR relative to trimethylphenylsilane as an external standard.

c

Isolated yield of the pure material was 86%.

d

No NaOAc was added.