An N-heterocyclic carbene-catalyzed switchable reaction of 9-(trimethylsilyl)fluorene and aldehydes: chemoselective synthesis of dibenzofulvenes and fluorenyl alcohols. Issue 16 (8th April 2021)

• Record Type: Journal Article
• Authors: Ma, Yu-Chuan; Luo, Jin-Yun; Zhang, Shi-Chu; Lu, Shu-Hui; Du, Guang-Fen; He, Lin
• Is Part Of: Organic & biomolecular chemistry. Volume 19:Issue 16(2021)
• Page Start: 3717
• Page End: 3721
• Publication Date: 2021-04-08
• Subjects: Chemistry, Organic -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1039/d1ob00065a
• Languages: English
• ISSNs: 1477-0520

Abstract

Abstract : N-Heterocyclic carbene-catalyzed chemoselective synthesis of dibenzofulvenes and fluorenyl alcohols via switchable reactions of 9-(trimethylsilyl)fluorene and aldehydes. Abstract : An N-heterocyclic carbene-catalyzed synthesis of dibenzofulvenes and fluorenyl alcohols was developed. In the presence of 10 mol% NHC (1, 3-bis(2, 6-diisopropylphenyl)imidazol-2-ylidene) and 4 Å molecular sieves, 9-(trimethylsilyl)fluorene undergoes an olefination reaction with aldehydes to produce dibenzofulvenes in 43–99% yields. However, on reducing the NHC loading to 1 mol% and with the addition of water, 9-(trimethylsilyl)fluorene selectively undergoes nucleophilic addition with aldehydes to afford fluorenyl alcohols in 40–95% yields.