The Palladium-Catalyzed Ullmann Cross-Coupling Reaction: A Modern Variant on a Time-Honored Process

Accounts of Chemical Research
Faiyaz KhanMartin G Banwell

Abstract

Cross-coupling reactions, especially those that are catalyzed by palladium, have revolutionized the way in which carbon-carbon bonds can be formed. The most commonly deployed variants of such processes are the Suzuki-Miyaura, Mizoroki-Heck, Stille, and Negishi cross-coupling reactions, and these normally involve the linking of an organohalide or pseudohalide (such as a triflate or nonaflate) with an organo-metallic or -metalloid such as an organo-boron, -magnesium, -tin, or -zinc species. Since the latter type of coupling partner is often prepared from the corresponding halide, methods that allow for the direct cross-coupling of two distinct halogen-containing compounds would provide valuable and more atom-economical capacities for the formation of carbon-carbon bonds. While the venerable Ullmann reaction can in principle achieve this, it has a number of drawbacks, the most significant of which is that homocoupling of the reaction partners is a competitive, if not the dominant, process. Furthermore, such reactions normally occur only under forcing conditions (viz., often at temperatures in excess of 250 °C). As such, the Ullmann reaction has seen only limited application in this regard, especially as a mid- to late-stage featur...Continue Reading

References

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Citations

Sep 17, 2019·Chemical Communications : Chem Comm·Bhushan MahajanAjay K Singh
Sep 24, 2020·Organic & Biomolecular Chemistry·Chengkou LiuKai Guo
Dec 4, 2020·Chemical & Pharmaceutical Bulletin·Tomoyuki YoshimuraJun-Ichi Matsuo
Jan 22, 2021·Organic & Biomolecular Chemistry·Xinxin LinKai Guo
Jan 13, 2021·Nature Communications·Kai WangZhang-Jie Shi
Jul 3, 2019·Accounts of Chemical Research·Xiao-Yu Liu, Yong Qin

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