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- W4308393924 abstract "Ring structures such as pyridine, cyclopentane or their combinations are important motifs in bioactive molecules. In contrast to previous cycloaddition reactions that necessitated a directly bonded initiating functional group, this work demonstrated a novel through-(hetero)arene radical transmission concept for selective activation of a remote bond. An efficient, metal-free and atom-economical [3+2] cycloaddition between 4-pyridinyl cyclopropanes and alkenes or alkynes has been developed for modular synthesis of pyridine-substituted cyclopentanes, cyclopentenes and bicyclo[2.1.1]hexanes that are difficult to access using known methods. This complexity-building reaction was catalyzed by a very simple and inexpensive diboron(4) compound and took place via dearomative/rearomative processes. The substrate scope was broad and more than 100 new compounds were prepared in generally high yields. Mechanistic experiments and density function theory (DFT) investigation supported a radical relay catalytic cycle involving alkylidene dihydropyridine radical intermediates and boronyl radical transfer." @default.
- W4308393924 created "2022-11-11" @default.
- W4308393924 creator A5014394467 @default.
- W4308393924 creator A5031870141 @default.
- W4308393924 creator A5036604252 @default.
- W4308393924 creator A5051427074 @default.
- W4308393924 creator A5073706747 @default.
- W4308393924 creator A5080102030 @default.
- W4308393924 creator A5083595315 @default.
- W4308393924 creator A5090654861 @default.
- W4308393924 date "2022-11-28" @default.
- W4308393924 modified "2023-10-16" @default.
- W4308393924 title "Diboron(4)‐Catalyzed Remote [3+2] Cycloaddition of Cyclopropanes via Dearomative/Rearomative Radical Transmission through Pyridine" @default.
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