{"doi":"10.1021/jacs.2c04779","title":"One-Step Synthesis of β-Alkylidene-γ-lactones via Ligand-Enabled β,γ-Dehydrogenation of Aliphatic Acids","abstract":"Ligand-enabled Pd-catalyzed regioselective α,β-dehydrogenation of carbonyl compounds via β-methylene C-H activation has recently emerged as a promising transformation. Herein, we report the realization of β,γ-dehydrogenation and subsequent vinyl C-H olefination reactions of free carboxylic acids, thus providing a unique method for the structural diversification of aliphatic acids containing α-quaternary centers through sequential functionalizations of two β-C-H bonds and one γ-C-H bond. This tandem dehydrogenation-olefination-lactonization reaction offers a one-step preparation of β-alkylidene-γ-lactones, which are often difficult to prepare through conventional methods, from inexpensive and abundant free aliphatic acids. A variety of free aliphatic acids, such as isosteviol and grandiflorolic acid natural products, and olefins are compatible with the reported protocol. The newly designed bidentate oxime ether-pyridone and morpholine-pyridone ligands are crucial for this tandem reaction to proceed. Notably, these ligands also enable preferential methylene C-H activation over the previously reported, competing process of methyl C-H bond olefination.","journal":"Journal of the American Chemical Society","year":2022,"id":236641,"datarank":0.0,"base_score":0.0,"endowment":0.0,"self_citation_contribution":0.0,"citation_network_contribution":0.0,"self_endowment_contribution":0.0,"citer_contribution":0.0,"corpus_percentile":null,"corpus_rank":null,"citation_count":67,"citer_count":0,"citers_with_citation_signal":0,"citers_with_endowment":0,"datacite_reuse_total":0,"is_dataset":false,"is_dataset_confidence":0.9434,"is_data_producer":false,"deposit_databanks":null,"is_oa":true,"file_count":0,"downloads":0,"has_version_chain":false,"published_date":"2022-01-01","fair_score":null,"fair_percentile":null,"algorithm_id":"datarank_citation_only_1hop_v6","ranking_scope":"data_only","authors":[{"id":351360,"name":"Zhe Zhuang","orcid":"0000-0001-6679-0496","position":1,"is_corresponding":false},{"id":857602,"name":"Zhen Wang","orcid":"0000-0001-8125-8019","position":2,"is_corresponding":false},{"id":857603,"name":"Liang Hu","orcid":"0000-0002-2960-9560","position":3,"is_corresponding":false},{"id":560144,"name":"Alastair N. Herron","orcid":"0000-0001-7141-3986","position":4,"is_corresponding":false},{"id":321502,"name":"Jennifer X. Qiao","orcid":"0000-0002-6685-2092","position":5,"is_corresponding":false},{"id":321507,"name":"Jin‐Quan Yu","orcid":"0000-0003-3560-5774","position":6,"is_corresponding":false},{"id":857601,"name":"Tao Sheng","orcid":"0000-0001-5339-9834","position":0,"is_corresponding":true}],"reference_count":38,"raw_metadata":null,"created_at":"2026-07-19T00:22:03.686498Z","pmid":"35802794","pmcid":null,"fwci":null,"citation_percentile":null,"influential_citations":0,"oa_status":null,"license":null,"views":0,"total_file_size_bytes":0,"version_count":0,"fair_f":null,"fair_a":null,"fair_i":null,"fair_r":null,"fair_zscore":null,"fair_rationale":null,"fair_model":null,"fair_agent_version":null,"fair_fulltext_source":null,"fair_has_llm":null,"fair_computed_at":null,"clinical_trials":[],"software_tools":[],"db_accessions":[],"linked_datasets":[],"topics":[]}