Thiol Ester−Boronic Acid Cross-Coupling. Catalysis Using Alkylative Activation of the Palladium Thiolate Intermediate

Author:

Savarin Cecile1,Srogl Jiri1,Liebeskind Lanny S.1

Affiliation:

1. Emory University, Department of Chemistry, 1515 Pierce Drive, Atlanta, Georgia 30322

Publisher

American Chemical Society (ACS)

Subject

Organic Chemistry,Physical and Theoretical Chemistry,Biochemistry

Reference10 articles.

1. Bio-organometallic Organosulfur Chemistry. Transi- tion Metal-Catalyzed Cross-Coupling Using Coen- zyme M or Thioglycolic Acid as the Leaving Group

2. Sulfonium Salts. Participants par Excellence in Metal-Catalyzed Carbon−Carbon Bond-Forming Reactions

3. TypicalProcedure:  2-Benzoyl-4-methoxybenzaldehyde, 7.A solution of 6%trans-di(μ-acetato)-bis[o-(di-o-tolylphosphino)benzyl]dipalladium(II) (14 mg, 0.03 mmol), K2CO3(313 mg, 2.27 mmol, 4.3 equiv), 33% NaI (26 mg, 0.17 mmol), 2-formyl-4-methoxyphenylboronic acid (113 mg, 0.62 mmol, 1.2 equiv) in dry and degassed dimethylacetamide (2 mL) was treated with 142 mg (0.52 mmol, 1.0 equiv) of thiol ester1afor 17 h at 95 °C to give 98 mg (0.41 mmol, 78%) of7as white needles. Mp 82−84 °C (Et2O−hexanes). Complete characterization data are listed in the Supporting Information.

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