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Synthesis 2022; 54(13): 3055-3068
DOI: 10.1055/a-1747-5457
DOI: 10.1055/a-1747-5457
paper
Base/B2pin2-Mediated Iodofluoroalkylation of Alkynes and Alkenes
We acknowledge the National Natural Science Foundation of China (Grant nos. 21861031, 21362025), Institute Local Cooperation Project of the Chinese Academy of Engineering (2019NXZD1), Key Research and Development Program of Ningxia (022104030009, 2021BEG02001, 2021BEE03003), and National First-rate Discipline Construction Project of Ningxia (Chemical Engineering and Technology) (NXYLXK2017A04).
Abstract
A base/B2pin2-mediated iodofluoroalkylation of alkynes and a part of alkenes, using ethyl difluoroiodoacetate (ICF2CO2Et) or ICnF2n+1 (n = 3, 4, 6) as difluoroacetylating or perfluoroalkylating reagent, is disclosed. The reaction proceeds under mild conditions, and iododifluoroalkylation, hydrodifluoroalkylation and several perfluoroalkylation products were generated from alkynes or alkenes. Notably, this methodology provides a simple access to difluoroalkylated and perfluoroalkylated organic compounds starting from simple alkynes or alkenes.
Key words
iodofluoroalkylation - alkynes - alkenes - ethyl 2,2-difluoro-2-iodoacetate - hydrodifluoroalkylationSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-1747-5457.
- Supporting Information
Publication History
Received: 18 November 2021
Accepted after revision: 21 January 2022
Accepted Manuscript online:
21 January 2022
Article published online:
19 May 2022
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Transition-metal-catalyzed fluoroalkylation of arenes methodologies:
Visible-light-catalyzed fluoroalkylation of arenes methodologies:
Radical initiator catalyzed fluoroalkylation of arenes methodologies: