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. Author manuscript; available in PMC: 2010 Dec 10.
Published in final edited form as: Chemistry. 2010 Feb 22;16(8):2355–2359. doi: 10.1002/chem.200902313

Table 2.

One-pot synthesis of unsymmetrical diaryl sulfides from two aryl bromides and HSTIPS catalyzed by Pd(OAc)2 and CyPF-tBu ligand.[a]

graphic file with name nihms253301u2.jpg
Products (Yield [%])
graphic file with name nihms253301t21.jpg2a (97%/98%[b]) graphic file with name nihms253301t22.jpg2b (97%) graphic file with name nihms253301t23.jpg2b (95%)
graphic file with name nihms253301t24.jpg2c (98%) graphic file with name nihms253301t25.jpg2d (98%) graphic file with name nihms253301t26.jpg2d (92%)[c]
graphic file with name nihms253301t27.jpg2e(91%) graphic file with name nihms253301t28.jpg2f (85%) graphic file with name nihms253301t29.jpg2g (95%)[d]
graphic file with name nihms253301t30.jpg2h (94%)[e] graphic file with name nihms253301t31.jpg2i(71%) graphic file with name nihms253301t32.jpg2j (77%)
graphic file with name nihms253301t33.jpg2k (69%)[f] graphic file with name nihms253301t34.jpg2l (92%) graphic file with name nihms253301t35.jpg2m (85%)[f]
[a]

All reactions were conducted with a 1:1 ratio of metal to ligand and 1 mmol of each aryl bromide and TIPS-SH.

[b]

0.25 mol% catalyst loading.

[c]

<5% of symmetrical sulfides were detected.

[d]

2.0 mol% catalyst loading.

[e]

3.0 mol% catalyst loading.

[f]

1.0 mol% catalyst loading.