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Synthesis 2023; 55(06): 907-918
DOI: 10.1055/a-1959-2742
DOI: 10.1055/a-1959-2742
special topic
Synthetic Advancements Enabled by Phosphorus Redox Chemistry
An Alternative to the Arbuzov Reaction: Generation and Transformation of α-Dialkyl-Substituted Methylphosphonate Carbanions via an SET Reduction Process
This work was supported by the Scientific Research Fund of the Department of Education of Zhejiang Province (No. Y202147855), the Natural Science Project of Zhejiang Pharmaceutical University (No. ZPCSR2020001), the Natural Science Foundation of Ningbo (No. 2021J140), and the Science and Technology Innovation 2025 Major Project of Ningbo (No. 2019B10112).
Abstract
With B-alkyl Suzuki cross-coupling as the strategy, 1-alkyl-substituted ethenylphosphonates could be efficiently accessed via palladium-catalyzed reactions of α-phosphonovinyl tosylates with B-alkyl-9-borabicyclo[3.3.1]nonane (B-alkyl-9-BBN). Using the α-alkylethenylphosphonates as radical acceptors, visible-light-driven photocatalytic Giese-type and cyclopropanation reactions based on reductive radical-polar crossover have been successfully developed. The redox-neutral photocatalysis serves as a viable strategy for the preparation of various 1,1-dialkyl-substituted methylphosphonates and 1-alkylcyclopropylphosphonates.
Key words
Suzuki reaction - redox-neutral photocatalysis - single-electron transfer - SET reduction - 1,1-dialkylmethylphosphonates - 1-alkylcyclopropylphosphonatesSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-1959-2742.
- Supporting Information
Publication History
Received: 31 July 2022
Accepted after revision: 12 October 2022
Accepted Manuscript online:
12 October 2022
Article published online:
22 November 2022
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