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. Author manuscript; available in PMC: 2020 Apr 5.
Published in final edited form as: ACS Catal. 2019 Mar 8;9(4):3716–3724. doi: 10.1021/acscatal.9b00091

Table 1.

Optimization of 3-Phenyloxindole Toluene Coupling (eq 12)

graphic file with name nihms-1020641-t0018.jpg
entry X Y additive (equiv) yield (%)b
1 0.3 2 98 (97)c
2 0.3 1 76
3 0.2 2 64
4 0.2 2 PivOH (1) 72
5 0.3 2 AcOH (1) 80
6 0.2 2 PivOH (1) 96d
7 0.3 2 AcOH (1) 77d
8 0.2 2 K2CO3 (1) 51
9 0.2 2 NaOAc (1) 44
a

Reaction conditions: 6a (0.15 mmol), 2a (0.1 M), Pd(OAc)2 (X mol %), K2S2O8 (Y equiv) at 120 oC for 24 h under argon.

b

Isolated yield.

c

Run twice

d

Activated charcoal (10x weight of Pd) was added.