Epoxides as Alkylating Reagents for the Catellani Reaction
Dr. Hong-Gang Cheng
College of Chemistry and Molecular Sciences, Wuhan University, Wuhan, 430072 China
Search for more papers by this authorChenggui Wu
College of Chemistry and Molecular Sciences, Wuhan University, Wuhan, 430072 China
Search for more papers by this authorHan Chen
College of Chemistry and Molecular Sciences, Wuhan University, Wuhan, 430072 China
These authors contributed equally.
Search for more papers by this authorRuiming Chen
College of Chemistry and Molecular Sciences, Wuhan University, Wuhan, 430072 China
These authors contributed equally.
Search for more papers by this authorGuangyin Qian
College of Chemistry and Molecular Sciences, Wuhan University, Wuhan, 430072 China
Search for more papers by this authorZhi Geng
College of Chemistry and Molecular Sciences, Wuhan University, Wuhan, 430072 China
Search for more papers by this authorQiang Wei
College of Chemistry and Molecular Sciences, Wuhan University, Wuhan, 430072 China
Search for more papers by this authorYuanyuan Xia
College of Chemistry and Molecular Sciences, Wuhan University, Wuhan, 430072 China
Search for more papers by this authorJingyang Zhang
College of Chemistry and Molecular Sciences, Wuhan University, Wuhan, 430072 China
Search for more papers by this authorYuming Zhang
College of Chemistry and Molecular Sciences, Wuhan University, Wuhan, 430072 China
Search for more papers by this authorCorresponding Author
Prof. Dr. Qianghui Zhou
College of Chemistry and Molecular Sciences, Wuhan University, Wuhan, 430072 China
The Institute for Advanced Studies, Wuhan University, Wuhan, 430072 China
Search for more papers by this authorDr. Hong-Gang Cheng
College of Chemistry and Molecular Sciences, Wuhan University, Wuhan, 430072 China
Search for more papers by this authorChenggui Wu
College of Chemistry and Molecular Sciences, Wuhan University, Wuhan, 430072 China
Search for more papers by this authorHan Chen
College of Chemistry and Molecular Sciences, Wuhan University, Wuhan, 430072 China
These authors contributed equally.
Search for more papers by this authorRuiming Chen
College of Chemistry and Molecular Sciences, Wuhan University, Wuhan, 430072 China
These authors contributed equally.
Search for more papers by this authorGuangyin Qian
College of Chemistry and Molecular Sciences, Wuhan University, Wuhan, 430072 China
Search for more papers by this authorZhi Geng
College of Chemistry and Molecular Sciences, Wuhan University, Wuhan, 430072 China
Search for more papers by this authorQiang Wei
College of Chemistry and Molecular Sciences, Wuhan University, Wuhan, 430072 China
Search for more papers by this authorYuanyuan Xia
College of Chemistry and Molecular Sciences, Wuhan University, Wuhan, 430072 China
Search for more papers by this authorJingyang Zhang
College of Chemistry and Molecular Sciences, Wuhan University, Wuhan, 430072 China
Search for more papers by this authorYuming Zhang
College of Chemistry and Molecular Sciences, Wuhan University, Wuhan, 430072 China
Search for more papers by this authorCorresponding Author
Prof. Dr. Qianghui Zhou
College of Chemistry and Molecular Sciences, Wuhan University, Wuhan, 430072 China
The Institute for Advanced Studies, Wuhan University, Wuhan, 430072 China
Search for more papers by this authorDedicated to Prof. Phil S. Baran and Prof. Dawei Ma
Graphical Abstract
A little cooperation can go a long way: A cooperative catalytic system comprising a PdII/XPhos complex and the potassium salt of 5-norbornene-2-carboxylic acid, which serves dual roles as a mediator and a base, enabled the use of epoxides as alkylating reagents in the Catellani reaction (see scheme). The products could also undergo oxa-Michael addition to furnish valuable isochroman scaffolds.
Abstract
We report a cooperative catalytic system comprising a PdII complex, XPhos, and the potassium salt of 5-norbornene-2-carboxylic acid that enables the use of epoxides as alkylating reagents in the Catellani reaction, thereby expanding the existing paradigm of this powerful transformation. The potassium salt of inexpensive 5-norbornene-2-carboxylic acid acts as both mediator and base in the process. This mild, chemoselective, scalable, and atom-economical protocol is compatible with a wide variety of readily available functionalized aryl iodides and epoxides, as well as terminating olefins. The resulting products undergo facile oxa-Michael addition to furnish ubiquitous isochroman scaffolds.
Supporting Information
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