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synthesis and catalytic functionalization of biologically active indoles

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PAPER Coupling Reactions <strong>of</strong> Electron-Rich Indoles 3725<br />

Table 2 Optimization <strong>of</strong> the Model Reaction <strong>of</strong> Indole 13 with o-Cresol a<br />

Br<br />

N<br />

OTBDMS<br />

Me<br />

+<br />

OH<br />

Entry Pd source Catalyst (mol%) Lig<strong>and</strong> 7 (mol%) Solvent Base Temperature (°C) Yield (%) b<br />

16<br />

13<br />

1 Pd(OAc) 2 0.5 1 toluene K 3PO 4 100 25<br />

2 Pd(OAc) 2 1 2 toluene K 3PO 4 100 34<br />

3 Pd(OAc) 2 2 4 toluene K 3PO 4 100 75<br />

4 Pd(OAc) 2 2 4 c toluene K 3PO 4 100 60<br />

5 Pd(OAc) 2 2 4 toluene K 3PO 4 120 83<br />

6 Pd(OAc) 2 2 4 toluene K 3PO 4 140 75<br />

7 Pd(OAc) 2 2 4 toluene K 3PO 4 160 71<br />

8 Pd 2dba 3 2 4 toluene K 3PO 4 100 44<br />

9 Pd 2dba 3 2 4 toluene K 3PO 4 120 38<br />

10 PdCl 2 2 4 toluene K 3PO 4 100

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