Regio- and Stereoselective Synthesis of Tri- and Tetrasubstituted Enamides via Palladium-Catalyzed Silaboration of Ynamides

• Published in: Advanced synthesis & catalysis Vol. 355; no. 5; pp. 853 - 856
• Main Authors: Saito, Nozomi, Saito, Keiichi, Sato, Hiroyasu, Sato, Yoshihiro
• Format: Journal Article
• Language: English
• Published: Weinheim WILEY-VCH Verlag 25.03.2013; WILEY‐VCH Verlag; Wiley
• Subjects: boron; Chemistry; Chemistry, Applied; Chemistry, Organic; metallation; palladium; Physical Sciences; Science & Technology; silicon; ynamides; C BOND-CLEAVAGE; N-ALLYL-YNAMIDES; REGIOSELECTIVE SILABORATION; TERMINAL ALKYNES; CLAISEN REARRANGEMENT; PLATINUM COMPLEXES; silicon; RING-CLOSING METATHESIS; ASYMMETRIC SILABORATION; metallation; palladium; ynamides; 2+2+2 CYCLOADDITIONS; STEREOGENIC CENTERS; boron
• ISSN: 1615-4150; 1615-4169
• DOI: 10.1002/adsc.201201111

The palladium‐catalyzed silaboration of ynamides is demonstrated. The silaboration proceeds in a highly regioselective manner to give the corresponding tri‐ and tetrasubstituted enamide derivatives having both a silyl group and a boryl group on the alkene. Furthermore, the silaborated enamide could be utilized as a coupling partner in Suzuki–Miyaura coupling with aryl iodides to give the corresponding cross‐coupling product in good yield.