期刊
ACS CATALYSIS
卷 10, 期 10, 页码 5821-5827出版社
AMER CHEMICAL SOC
DOI: 10.1021/acscatal.0c01199
关键词
epoxides; arylation; cross-electrophile coupling; photoredox catalysis; nickel catalysis; titanium catalysis; radical chemistry; photochemistry
资金
- Pfizer
- NIGMS [5R35GM126986-02]
- NIH [1F32GM129910-01A1]
A cross-electrophile coupling reaction of epoxides and (hetero)aryl iodides that operates via the merger of three catalytic cycles involving a Ni-, Ti-, and organic photoredox catalyst has been developed. Three distinct classes of epoxides, styrene oxides, cyclic epoxides, and terminal aliphatic epoxides, all undergo coupling in moderate to good yield and high regioselectivity with the use of three different nitrogen-based ligands for Ni under otherwise identical reaction conditions. The mild reaction conditions accommodate a broad scope of abundant and complex coupling partners. Mechanistic studies suggest that when styrene oxides are employed radical intermediates are involved via Ti-radical ring-opening of the epoxide. Conversely, for terminal aliphatic epoxides, involvement of an iodohydrin intermediate enables the formation of the unexpected linear product.
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