Imidazotetrazines as Weighable Diazomethane Surrogates for Esterifications and Cyclopropanations.
Imidazotetrazines as Weighable Diazomethane Surrogates for Esterifications and Cyclopropanations.
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DOI：
10.1002/anie.201911896
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发表时间：
2019-12
影响因子：
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通讯作者：
Riley L. Svec;P. Hergenrother
中科院分区：
文献类型：
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作者：
Riley L. Svec;P. Hergenrother
Diazomethane is one of the most versatile reagents in organic synthesis, but its utility is limited by its hazardous nature. Although alternative methods exist to perform the unique chemistry of diazomethane, these suffer from diminished reactivity and/or correspondingly harsher conditions. Here we describe the repurposing of imidazotetrazines (such as temozolomide, TMZ, the standard of care for glioblastoma) for use as synthetic precursors of alkyl diazoniums. TMZ is employed to conduct esterifications and metal-catalyzed cyclopropanations, and results show that methyl ester formation from a wide variety of substrates is especially efficient and operationally simple. TMZ is a commercially available solid that is non-explosive and non-toxic, and should find broad utility as a replacement for diazomethane.
