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. Author manuscript; available in PMC: 2020 Jun 7.
Published in final edited form as: Org Lett. 2019 Mar 21;21(11):3886–3890. doi: 10.1021/acs.orglett.9b00779

Table 1.

Reaction Parameters for Annulation to 10aaaa

graphic file with name nihms-1026426-t0010.jpg

entry variation Yield %b
1 none 73 (74)c
2 0.1 mmol 5a + 2 equiv 8a +1.5 equiv 9a 55
3 [Cp*RliCl2]2 (5%) 65
4 no Rh   0
5 PivOH (1 equiv) 71
6 PivOH (0.5 equiv) 68
7 no PivOH 48
8 AcOH instead of PivOH 57
9 no NaOAc 60
10 150 °C 73
11 TFE as solvent 70
12 EtOH as solvent 10
13 dioxane as solvent   4
14 0.4 M 61
15 0.1 M 74
16 [Cp*Rh(MeCN)3](SbF6)2 (5%) 72
17 [Cp*Rh(MeCN)3](SbF6)2(2%), 150 °C 65
18 no sieves 68
19 conventional heating, 100 °C, 20 h 70 (72%)c
20 [Cp*Co(MeCN)3](SbF6)2 (10%)   0
21 [Cp*IrCl2]2 (5%) and AgSbF6 (20%) 72
a

Conditions: 8a (0.10 mmol), 5a (0.20 mmol), 9a (0.15 mmol).

b

Yields determined by 1H NMR integration relative to 1,3,5-trimethoxybenzene as external standard.

c

Isolated yield at 0.30 mmol scale of limiting reagent 8a.