C–H Alkylation of Heteroarenes with Tertiary and Secondary Alkyl Bromides

Irradiation-Induced Palladium-Catalyzed Direct C–H Alkylation of Heteroarenes with Tertiary and Secondary Alkyl Bromides: G.-Z. Wang, R. Shang, Y, Fu
Synthesis 2018, DOI: 10.1055/s-0036-1592000

Incorporation of secondary and tertiary alkyl functions, such as cycloalkyl rings or terbutyl/adamantyl groups, onto heterocycles can be a challenging process owing to the proclivity of secondary and tertiary halides – which are the most common alkylating agents – to undergo elimination rather than addition. Recently, Professor Rui Shang from The University of Tokyo (Japan) and the group of Professor Fu from the University of Science and Technology of China, Hefei (P. R. of China) reported a new efficient and broadly applicable process for achieving this transformation.

Professor Shang said: “Although most palladium-catalyzed C–H functionalizations use their organometallic reactivity under thermal conditions, the work presented herein demonstrates a new opportunity to operate palladium-catalyzed C–H alkylation under visible-light irradiation through a hybrid alkyl Pd(I) radical intermediate.”
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