C(sp 3 )–H methylation enabled by peroxide photosensitization and Ni-mediated radical coupling | Zendy

Aristidis Vasilopoulos | Zendy; Shane W. Krska | Zendy; Shan S. Stahl | Zendy

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C(sp ³ )–H methylation enabled by peroxide photosensitization and Ni-mediated radical coupling

Author(s) -

Aristidis Vasilopoulos,

Shane W. Krska,

Shan S. Stahl

Publication year - 2021

Publication title -

science

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 12.556

H-Index - 1186

eISSN - 1095-9203

pISSN - 0036-8075

DOI - 10.1126/science.abh2623

Subject(s) - cleave , radical , peroxide , methylation , chemistry , catalysis , substrate (aquarium) , photochemistry , aryl , molecule , organic peroxide , medicinal chemistry , combinatorial chemistry , stereochemistry , organic chemistry , enzyme , biochemistry , copolymer , biology , dna , ecology , alkyl , polymer

Adding methyl groups with good timing In pharmaceutical research, swapping out hydrogens for methyl groups is a frequent strategy to optimize small-molecule properties. Vasilopouloset al. report a versatile, convenient, and comparatively safe method for methylation of carbon centers adjacent to nitrogen or aryl rings. Under carefully optimized conditions, di-tert-butyl peroxide plays a dual role as oxidant and methyl source. Cleaving the O–O bond through photosensitization produces butoxyl radicals, some of which cleave substrate C–H bonds, whereas others release methyl radicals that a nickel catalyst delivers to those activated substrates.Science , this issue p.398

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