Palladium-catalyzed coupling reaction of 2-iodobiphenyls with alkenyl bromides for the construction of 9-(diorganomethylidene)fluorenes. Issue 38 (14th September 2021)

• Record Type: Journal Article
• Authors: Zhao, Ya-Heng; Wang, Jian-Long; Zhou, Yun-Bing; Liu, Miao-Chang; Wu, Hua-Yue
• Is Part Of: Organic & biomolecular chemistry. Volume 19:Issue 38(2021)
• Page Start: 8250
• Page End: 8253
• Publication Date: 2021-09-14
• Subjects: Chemistry, Organic -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1039/d1ob01547h
• Languages: English
• ISSNs: 1477-0520

Abstract

Abstract : An atom economical protocol for the construction of 9-(diorganomethylidene)fluorenes through palladium-catalyzed coupling reactions of 2-iodobiphenyls with alkenyl bromides has been reported. Abstract : An atom economical protocol for the construction of 9-(diorganomethylidene)fluorenes through palladium-catalyzed coupling reactions of 2-iodobiphenyls with alkenyl bromides has been reported. The reaction proceeds through the C–H activation/oxidative addition/reduction elimination/intramolecular Heck coupling reaction to afford a series of 9-(diorganomethylidene)fluorenes with good yields. Control experiments demonstrate that a five-membered palladacycle acts as a key intermediate and β-H elimination serves as the rate-limiting step.