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Nickel-Catalyzed Reductive Csp2-Csp3 Cross Coupling Using Phosphonium Salts
Huifei Wang1,2,3, Mengwan Yang1, Yuting Wang1
1Key Laboratory of Advanced Mass Spectrometry and Molecular Analysis of Zhejiang Province, School of Material Science and Chemical Engineering, Ningbo University, Ningbo 315211, China.
Organic Letters
|October 19, 2021
Summary
A new nickel-catalyzed reaction enables the direct formation of carbon-carbon bonds using phosphonium salts and allylic electrophiles. This method offers broad compatibility, even with challenging heterocyclic compounds.
Area of Science:
- Organic Chemistry
- Catalysis
- Synthetic Methodology
Background:
- Carbon-carbon bond formation is fundamental in organic synthesis.
- Reductive cross-coupling reactions offer efficient pathways for C-C bond construction.
- Developing novel catalytic systems for challenging coupling reactions remains an active area of research.
Purpose of the Study:
- To develop a novel nickel-catalyzed reductive cross-coupling protocol.
- To enable the direct construction of C(sp2)-C(sp3) bonds.
- To achieve coupling with phosphonium salts and allylic C(sp3)-O bond electrophiles.
Main Methods:
- Nickel-catalyzed reductive cross-coupling reaction.
- Utilized phosphonium salts and allylic C(sp3)-O bond electrophiles as substrates.
- Investigated reaction conditions for optimal yield and selectivity.
Main Results:
- Successfully developed a nickel-catalyzed reductive cross-coupling protocol.
- Demonstrated direct construction of the C(sp2)-C(sp3) bond.
- Achieved broad substrate scope, high functional-group tolerance, and heterocycle compatibility.
- First-time accomplishment of reductive cross-coupling with heterocyclic thiazolylphosphonium salts.
Conclusions:
- The developed protocol provides an efficient method for C(sp2)-C(sp3) bond formation.
- The reaction exhibits excellent functional group tolerance and compatibility with heterocycles.
- This work expands the scope of reductive cross-coupling reactions, particularly for challenging heterocyclic substrates.
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