Secondary benzylation with benzyl alcohols catalyzed by a high-valent heterobimetallic Ir-Sn complex.
A highly efficient secondary benzylation procedure has been demonstrated using a high-valent heterobimetallic complex [Ir2(COD)2(SnCl3)2(Cl)2(mu-Cl)2] 1 as the catalyst in 1,2-dichloroethane to afford the corresponding benzylated products in moderate to excellent yields. The reaction was performed not only with carbon nucleophiles (arenes and heteroarenes) but also with oxygen (alcohol), nitrogen (amide and sulfonamide), and sulfur (thiol) nucleophiles. Mechanistic investigation showed the intermediacy of the ether in this reaction. An electrophilic mechanism is proposed from Hammett correlation.
Podder
Susmita
S
Organometallics & Catalysis Laboratory, Department of Chemistry, Indian Institute of Technology, Kharagpur 721302, India.
Choudhury
Joyanta
J
Roy
Sujit
S
D001554:Benzene / Q000737:chemistry*; D001592:Benzyl Alcohols / Q000737:chemistry*; D002384:Catalysis; D007495:Iridium / Q000737:chemistry*; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000737:chemistry*; D013237:Stereoisomerism; D013457:Sulfur Compounds; D014001:Tin / Q000737:chemistry*
D001592:Benzyl Alcohols; D009942:Organometallic Compounds; D013457:Sulfur Compounds; D007495:Iridium; D014001:Tin; D001554:Benzene