期刊
JOURNAL OF ORGANIC CHEMISTRY
卷 80, 期 1, 页码 223-236出版社
AMER CHEMICAL SOC
DOI: 10.1021/jo5023102
关键词
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资金
- National Basic Research Program of China (973 Program) [2015CB856600]
- National Natural Science Foundation of China [21272010, 21332002]
Ir(III)-catalyzed coupling of aromatic C-H bonds with diazomalonates has been achieved successfully via a metal carbene migratory insertion process. With different types of carbamoyl directing groups, a wide range of arenes, including heteroarenes, can be used as substrates in this Ir(III)-catalyzed C-H functionalization reaction. Mono- and bisfunctionalized products can be obtained selectively simply by changing the number of equivalents of the diazo substrate. Moreover, when diazomalonates bearing one or two tert-butyl groups are used as the substrates, the C-H bond functionalization is followed by decarboxyation, leading to products with a -CH2CO2Me or -CH2CO2H moiety at the position ortho to the directing group. This reaction demonstrates that direct C-H activation and the metal carbene migratory insertion can be merged into one catalytic cycle with an Ir(III) complex as the catalyst.
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