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When tetrahydrocarbazoles and heteroatom-replaced (O and N) analogues were employed, oxidative rearrangement proceeded smoothly to afford spiro-3-oxoindolines. The reaction solvent DMSO worked as a green and quantitative reductant, avoiding the traditional utilization of a stoichiometric phosphine. Converting to tetrahydrocyclopenta[b]indole derivatives, a selective oxidative C(sp2)-C(sp2) bond cleavage was also illustrated, enabling conversion to eight-membered-ring lactams. The preliminary investigation of flammability and explosion risks, combined with kinetic analysis, provides valuable insights into this oxidation reaction. A selective anti-breast-tumor agent 11b against MCF-7 could be formed in 93% yield via Suzuki coupling.<\/jats:p>","DOI":"10.1021\/acs.joc.6c01133","type":"journal-article","created":{"date-parts":[[2026,9,12]],"date-time":"2026-09-12T03:01:40Z","timestamp":1789182100000},"page":"12902-12911","source":"Crossref","is-referenced-by-count":0,"title":["Substrate-Controlled\nConstruction of Spiro-3-Oxoindolines\nand Eight-Membered-Ring Lactams under Bubbling Air Conditions"],"prefix":"10.1021","volume":"91","author":[{"given":"Xiao","family":"Zhang","sequence":"first","affiliation":[{"name":"East China University of Science and Technology , , 130 Meilong Road , ,","place":["Shanghai, China, 200237"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Jiahao","family":"Zhang","sequence":"additional","affiliation":[{"name":"University of Nottingham Ningbo , , China, 199 Taikang East Road , ,","place":["Ningbo, P. R. 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