Literature DB >> 30123905

Synthesis of acyl fluorides via photocatalytic fluorination of aldehydic C-H bonds.

Michael Meanwell1, Johannes Lehmann1, Marc Eichenberger2, Rainer E Martin2, Robert Britton1.   

Abstract

Acyl fluorides are versatile acylating agents owing to their unique stability. Their synthesis, however, can present challenges and is typically accomplished through deoxyfluorination of carboxylic acids. Here, we demonstrate that acyl fluorides can be prepared directly from aldehydes via a C(sp2)-H fluorination reaction involving the inexpensive photocatalyst sodium decatungstate and electrophilic fluorinating agent N-fluorobenzenesulfonimide. This convenient fluorination strategy enables direct conversion of aliphatic and aromatic aldehydes into acylating agents.

Entities:  

Year:  2018        PMID: 30123905     DOI: 10.1039/c8cc06375c

Source DB:  PubMed          Journal:  Chem Commun (Camb)        ISSN: 1359-7345            Impact factor:   6.222


  6 in total

1.  N-Hydroxybenzimidazole as a structurally modifiable platform for N-oxyl radicals for direct C-H functionalization reactions.

Authors:  Tomomi Yoshii; Saori Tsuzuki; Shunya Sakurai; Ryu Sakamoto; Julong Jiang; Miho Hatanaka; Akira Matsumoto; Keiji Maruoka
Journal:  Chem Sci       Date:  2020-05-18       Impact factor: 9.825

Review 2.  Photoredox-Catalyzed C-H Functionalization Reactions.

Authors:  Natalie Holmberg-Douglas; David A Nicewicz
Journal:  Chem Rev       Date:  2021-09-29       Impact factor: 60.622

3.  Luminescent tungsten(vi) complexes as photocatalysts for light-driven C-C and C-B bond formation reactions.

Authors:  Daohong Yu; Wai-Pong To; Glenna So Ming Tong; Liang-Liang Wu; Kaai-Tung Chan; Lili Du; David Lee Phillips; Yungen Liu; Chi-Ming Che
Journal:  Chem Sci       Date:  2020-05-25       Impact factor: 9.825

4.  Deoxyfluorination of acyl fluorides to trifluoromethyl compounds by FLUOLEAD®/Olah's reagent under solvent-free conditions.

Authors:  Yumeng Liang; Akihito Taya; Zhengyu Zhao; Norimichi Saito; Norio Shibata
Journal:  Beilstein J Org Chem       Date:  2020-12-14       Impact factor: 2.883

5.  [3+2] Cycloaddition of alkyl aldehydes and alkynes enabled by photoinduced hydrogen atom transfer.

Authors:  Siya Le; Ji Li; Jian Feng; Zuxiao Zhang; Yihui Bai; Zheliang Yuan; Gangguo Zhu
Journal:  Nat Commun       Date:  2022-08-12       Impact factor: 17.694

Review 6.  Direct Photocatalyzed Hydrogen Atom Transfer (HAT) for Aliphatic C-H Bonds Elaboration.

Authors:  Luca Capaldo; Davide Ravelli; Maurizio Fagnoni
Journal:  Chem Rev       Date:  2021-08-06       Impact factor: 60.622

  6 in total

北京卡尤迪生物科技股份有限公司 © 2022-2023.