Straightforward Synthesis of Alkyl Fluorides via Visible-Light-Induced Hydromono- and Difluoroalkylations of Alkenes with α-Fluoro Carboxylic Acids

Abstract

We herein report the first visible-light-induced hydromono-and difluoroalkylations of alkenes with inexpensive and easily accessible α-fluoro carboxylic acids. This metal-free protocol exhibits mild conditions, high efficiency, and excellent functional-group tolerance, providing a straightforward approach to mono-and difluoroalkylated alkanes. Moreover, the fluorine effect on the hydrofluoroalkylation reaction is discussed in detail.

Rh(III)‐Catalyzed Annulative Coupling of Sulfoxonium Ylides with Allyl Acetates: Generation of Bicyclo[4.1.0]heptan‐2‐ones

“…Additional references cited within the Supporting Information. [14,[17][18][19][20][21][22][23][24][25][26][27]…”

“…The date that support the findings of this study are available in the supplementary material of this article. Additional references cited within the Supporting Information [14,17–27] …”

Transformations based on direct excitation of hypervalent iodine(iii) reagents

“…37 In 2022 Li performed a similar radical addition with fluoroalkyl radicals and THF as a hydrogen donor under blue LEDs irradiation (Scheme 4B). 38 The reaction gives easy access to valuable fluorinated products from the substrates with unacti-vated terminal double bonds. Liu, Zhou, and Lu developed a hydrodifluoroalkylation reagent which enabled them to functionalize different unactivated alkenes and also alkynes (Scheme 4C).…”

Photoredox-catalyzed direct C–H monofluoromethylation of heteroarenes

“…11,23 Notably, hypervalent iodine( iii ) reagents have quickly emerged as efficient fluoroalkyl radical partners for a wide array of carbon–carbon bond-forming reactions promoted by visible-light photoredox catalysis. 24–29…”