Allylsulfones through Palladium‐Catalyzed Allylic C−H Sulfonylation of Terminal Alkenes. Issue 8 (26th January 2023)

• Record Type: Journal Article
• Authors: Chen, Tingting; Lahbi, Jassmin; Broggini, Gianluigi; Pradal, Alexandre; Poli, Giovanni
• Is Part Of: European journal of organic chemistry. Volume 26:Issue 8(2023)
• Page Start: n/a
• Page End: n/a
• Publication Date: 2023-01-26
• Subjects: allylsulfones -- C−H activation -- one-pot sequential reactions -- palladium catalysis -- sulfonylation; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.202201493
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract: Two previously unknown protocols for Pd‐catalyzed allylic C−H sulfonylation of terminal alkenes have been developed. While the former consists of a direct Pd(II)‐catalyzed oxidative C−H allylic sulfonylation in the presence of sulfinate anions, the latter involves a sequential one‐pot Pd(II)‐catalyzed C−H allylic acetoxylation followed by a Pd(0)‐catalyzed sulfonylation. The scope of both protocols was studied on 25 examples. Abstract : We report two distinct protocols for the preparation of allylsulfones via Pd(II)‐catalyzed allylic C−H activation. While the former protocol consists of a direct Pd(II)‐catalyzed oxidative C−H allylic sulfonylation in the presence of sulfinate anions, the latter involves a sequential one‐pot Pd(II)‐catalyzed C−H allylic acetoxylation followed by a Pd(0)‐catalyzed sulfonylation.