Palladium-Catalyzed CH Activation and Intermolecular Annulation with Allenes

• Published in: Chemistry : a European journal Vol. 20; no. 17; pp. 5087 - 5091
• Main Authors: Xia, Xiao-Feng, Wang, Yu-Qi, Zhang, Lu-Lu, Song, Xian-Rong, Liu, Xue-Yuan, Liang, Yong-Min
• Format: Journal Article
• Language: English
• Published: Weinheim WILEY-VCH Verlag 22.04.2014; WILEY‐VCH Verlag; Wiley
• Subjects: allenes; annulation; Chemical reactions; Chemistry; Chemistry, Multidisciplinary; Compatibility; CH activation; Functional groups; Isotope effect; Moisture; Organic chemistry; palladium; Physical Sciences; Science & Technology; Synthesis; synthetic methods; Terminals; PD(II)-CATALYZED ORTHO; FUNCTIONALLY-SUBSTITUTED ARYL; ARYLATION; ARENES; allenes; annulation; CH activation; OLEFINATION; CARBOANNULATION; palladium; N BOND FORMATION; HETEROANNULATION; synthetic methods; CH activation
• ISSN: 0947-6539; 1521-3765
• DOI: 10.1002/chem.201304300

A new and efficient PdII‐catalyzed intermolecular annulation of N‐benzoylsulfonamide with allenes for the synthesis of 3,4‐dihydroisoquinolin‐1(2H)‐ones is reported. This CH functionalization is compatible with ambient air and moisture, and it can be applied to terminal or internal allenes with different synthetically attractive functional groups. Control experiments and a kinetic isotope effect study are conducted and a plausible mechanism is proposed. A new and efficient PdII‐catalyzed intermolecular annulation of N‐benzoylsulfonamide with allenes for the synthesis of 3,4‐dihydroisoquinolin‐1(2H)‐ones is reported (see scheme). This CH functionalization is compatible with ambient air and moisture, and it can be applied to terminal or internal allenes with different synthetically attractive functional groups. Control experiments and a kinetic isotope effect study were conducted and a plausible mechanism is proposed.