{"database":"biostudies-literature","file_versions":[],"scores":null,"additional":{"submitter":["Ni HQ"],"funding":["National Institutes of Health","NIGMS NIH HHS"],"pagination":["e202114346"],"full_dataset_link":["https://www.ebi.ac.uk/biostudies/studies/S-EPMC8923970"],"repository":["biostudies-literature"],"omics_type":["Unknown"],"volume":["61(13)"],"pubmed_abstract":["In this study, we systematically evaluate different ambiphilic organohalides for their ability to participate in anti-selective carbo- or heteroannulation with non-conjugated alkenyl amides under Pd<sup>II</sup> /Pd<sup>IV</sup> catalysis. Detailed optimization of the reaction conditions has led to protocols for synthesizing tetrahydropyridines, tetralins, pyrrolidines, and other carbo/heterocyclic cores via [n+2] (n=3-5) (hetero)annulation. Expansion of scope to otherwise unreactive ambiphilic haloketones through Pd<sup>II</sup> /amine co-catalysis is also demonstrated. Compared to other annulation processes, this method proceeds via a distinct Pd<sup>II</sup> /Pd<sup>IV</sup> mechanism involving Wacker-type directed nucleopalladation. This difference results in unique reactivity and selectivity patterns, as revealed through assessment of reaction scope and competition experiments."],"journal":["Angewandte Chemie (International ed. in English)"],"pubmed_title":["Mapping Ambiphile Reactivity Trends in the Anti-(Hetero)annulation of Non-Conjugated Alkenes via Pd<sup>II</sup> /Pd<sup>IV</sup> Catalysis."],"pmcid":["PMC8923970"],"funding_grant_id":["5R35GM125052-05","3R35GM125052-04S2","R35 GM125052"],"pubmed_authors":["McAlpine IJ","Bedekar PG","Ni HQ","Sach N","Wang F","Engle KM","Cooper P","Tran-Dube M","Yang S","Donaldson JS"],"additional_accession":[]},"is_claimable":false,"name":"Mapping Ambiphile Reactivity Trends in the Anti-(Hetero)annulation of Non-Conjugated Alkenes via Pd<sup>II</sup> /Pd<sup>IV</sup> Catalysis.","description":"In this study, we systematically evaluate different ambiphilic organohalides for their ability to participate in anti-selective carbo- or heteroannulation with non-conjugated alkenyl amides under Pd<sup>II</sup> /Pd<sup>IV</sup> catalysis. Detailed optimization of the reaction conditions has led to protocols for synthesizing tetrahydropyridines, tetralins, pyrrolidines, and other carbo/heterocyclic cores via [n+2] (n=3-5) (hetero)annulation. Expansion of scope to otherwise unreactive ambiphilic haloketones through Pd<sup>II</sup> /amine co-catalysis is also demonstrated. Compared to other annulation processes, this method proceeds via a distinct Pd<sup>II</sup> /Pd<sup>IV</sup> mechanism involving Wacker-type directed nucleopalladation. This difference results in unique reactivity and selectivity patterns, as revealed through assessment of reaction scope and competition experiments.","dates":{"release":"2022-01-01T00:00:00Z","publication":"2022 Mar","modification":"2025-04-05T16:11:09.236Z","creation":"2025-04-05T16:11:09.236Z"},"accession":"S-EPMC8923970","cross_references":{"pubmed":["35007393"],"doi":["10.1002/anie.202114346"]}}