Intramolecular chaperone-assisted dual-anchoring activation (ICDA): a suitable preorganization for electrophilic halocyclization
Xihui Yang,
Haowei Gao,
Jiale Yan
et al.
Abstract:Halocyclization reaction represents one of the most common methodologies for the synthesis of heterocyclic molecules. Many efforts have been developed to balance the relationship between structure, reactivity and selectivity, including...
“…More recently, our group disclosed that the simultaneous use of cyclic diacyl peroxides and halide salts could facilitate the direct generation of heteroatom-centered radicals and electrophilic halocyclization through spatial-confinement non-covalent orientation and intramolecular carboxylate-assisted proximity effects, respectively. 14 All the aforementioned studies indicate that strained cyclic diacyl peroxides and acyclic diacyl peroxides exhibit fundamentally different characteristics, although they share similarities in atom connectivity.…”
Herein, we have developed an efficient PdII-catalyzed intramolecular oxidative C–H amination under additive-free and green conditions where strained cyclic diacyl peroxide functions as both a sacrificial oxidant and a bidentate linker.
“…More recently, our group disclosed that the simultaneous use of cyclic diacyl peroxides and halide salts could facilitate the direct generation of heteroatom-centered radicals and electrophilic halocyclization through spatial-confinement non-covalent orientation and intramolecular carboxylate-assisted proximity effects, respectively. 14 All the aforementioned studies indicate that strained cyclic diacyl peroxides and acyclic diacyl peroxides exhibit fundamentally different characteristics, although they share similarities in atom connectivity.…”
Herein, we have developed an efficient PdII-catalyzed intramolecular oxidative C–H amination under additive-free and green conditions where strained cyclic diacyl peroxide functions as both a sacrificial oxidant and a bidentate linker.
Two cascade approaches featuring bromocycloetherification-elimination or dehydrogenative cycloetherification-isomerization of lactam-tethered alkenols have facilitated the stereocontrolled synthesis of lactam-fused 3-methylenetetrahydropyrans.
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