Palladium Pincer Complex Catalyzed Substitution of Vinyl Cyclopropanes, Vinyl Aziridines, and Allyl Acetates with Tetrahydroxydiboron. An Efficient Route to Functionalized Allylboronic Acids and Potassium Trifluoro(allyl)borates

Sara Sebelius, Vilhelm J. Olsson and Kálmán J. Szabó*

*Department of Organic Chemistry, Stockholm University, SE-106 91 Stockholm, Sweden, Email: kalmanorgan.su.se

S. Sebelius, V. J. Olsson, K. J. Szabó, J. Am. Chem. Soc., 2005, 127, 10478-10479.

DOI: 10.1021/ja052885q

---

Abstract

A mild, selective, palladium-catalyzed boronation of vinyl cyclopropane, vinyl aziridine, and allyl acetate substrates could be accomplished using tetrahydroxydiboron in the presence of a palladium pincer complex catalyst to give synthetically useful linear trifluoro(allyl)borates or allyl boronates incorporating a trans double bond. Functionalities such as Br, COOEt, ArSO₂(NH), OAc, and SiRMe₂ are tolerated.

see article for more examples

---

---

Direct Synthesis of Functionalized Allylic Boronic Esters from Allylic Alcohols and Inexpensive Reagents and Catalysts

G. Dutheuil, N. Selander, K. J. Szabó, V. K. Aggarwal, Synthesis, 2008, 2293-2297.

Direct Boronation of Allyl Alcohols with Diboronic Acid Using Palladium Pincer-Complex Catalysis. A Remarkably Facile Allylic Displacement of the Hydroxy Group under Mild Reaction Conditions

V. J. Olsson, S. Sebelius, N. Selander, K. J. Szabó, J. Am. Chem. Soc., 2006, 128, 4588-4589.

Direct Boronation of Allyl Alcohols with Diboronic Acid Using Palladium Pincer-Complex Catalysis. A Remarkably Facile Allylic Displacement of the Hydroxy Group under Mild Reaction Conditions

V. J. Olsson, S. Sebelius, N. Selander, K. J. Szabó, J. Am. Chem. Soc., 2006, 128, 4588-4589.

---

Key Words

Potassium Allyltrifluoroborates

---

ID: J48-Y2005-2500