A Cross-Coupling Reaction between Ortho-Substituted Aryl Iodide and Diazoester Using Tri-(2-furyl)phosphine as a
Kazuki Naoi1, Shinji Nagumo1,2
1Applied Chemistry and Chemical Engineering, Graduate School of Engineering, Kogakuin University, Nakano 2665-1, Hachioji, Tokyo 192-0015, Japan.
Abstract:
A palladium-complex-catalyzed cross-coupling reaction was achieved between benzyl diazo esters and aryl iodides bearing ortho-substituents, which had previously not been tolerated for such reactions. In the quest for an optimal catalyst for reactions with ortho-iodobenzaldehyde, the yields of the desired coupling compound were unsatisfactory in many catalyst systems, and the aldol reaction frequently occurred competitively. However, the catalyst prepared from Pd(dba)2 and P(2-furyl)3 promoted the cross-coupling reaction, generating α-diazophenyl acetate in excellent yield. The cross-coupling was also acceptable for aryl iodides with various ortho-substituents, delivering a variety of coupling products in moderate to good yields.
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