Ylide‐Functionalized Diisopropyl Phosphine (prYPhos): A Ligand for Selective Suzuki‐Miyaura Couplings of Aryl Chlorides. Issue 19 (8th June 2022)

• Record Type: Journal Article
• Authors: Wei, Xiao‐Jing; Xue, Bingxiang; Handelmann, Jens; Hu, Zhiyong; Darmandeh, Heidar; Gessner, Viktoria H.; Gooßen, Lukas J.
• Is Part Of: Advanced synthesis & catalysis. Volume 364:Issue 19(2022)
• Page Start: 3336
• Page End: 3341
• Publication Date: 2022-06-08
• Subjects: YPhos ligand -- Suzuki-Miyaura coupling -- Chemoselective coupling -- Ligand development -- Palladium catalysis; Catalysis -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Chemistry -- Periodicals; Chemistry, Technical -- Periodicals; Chemistry -- Periodicals; Catalysis -- Periodicals; Technology, Pharmaceutical -- Periodicals; 547.2
• DOI: 10.1002/adsc.202200321
• Languages: English
• ISSNs: 1615-4150

Abstract

Abstract: The ylide‐functionalized diisopropyl phosphine (prYPhos) promotes Pd‐catalyzed Suzuki‐Miyaura couplings of aryl chlorides and bromides with arylboronic acids. Using Pd2 (dba)3 /prYPhos as the catalyst and K2 CO3 as the base, various (hetero)biaryls were synthesized in 45–98% yields at mild reaction conditions, tolerating sensitive functional groups and steric hindrance. The electron rich, sterically demanding ligand induces a high selectivity for halides versus triflate. Chloroaryl triflates were selectively coupled at the chloride, leaving inherently more reactive triflate groups in place. Abstract :