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A.","year":"2017","journal-title":"Chim. Oggi-Chem. Today"},{"key":"ref22\/cit22","unstructured":"Other terminal oxidants\nwere\nalso considered for this coupling (Cu(OAc)2, CuCl2, AgCO3, Ag2O, DMBQ, PIDA, BQ, Oxone\u00ae,\nH2O2, t-BuO2H, AgNO3 and\nK2S2O8). However, none of these oxidants\nperformed better than AgOAc."},{"key":"ref24\/cit24","unstructured":"Preparation\nof compound 3ab was also performed on a 16.2 mmol scale\nproviding the\ndesired product with 47% isolated yield and a d.r. of 69:31."},{"key":"ref25\/cit25","unstructured":"The low yield of 3af and 3ag was due to difficulties to separate\nthe product\nfrom the starting acrylate during purification."},{"key":"ref26\/cit26","unstructured":"We only considered tertiary acrylamides,\nas primary and secondary acrylamides are expected to be incompatible\nwith this coupling."},{"key":"ref27\/cit27","unstructured":"The low yield of this product\nis mainly due its high volatility."},{"key":"ref28\/cit28","unstructured":"Other electron-poor alkene partners\nsuch as acrylonitrile, phenylvinylsulfoxide, vinyl diethylphosphonate\nor 5,6-dihydro-2H-pyran-2-one did not provide the\ndesired coupling product. No conversion was observed with acrylonitrile\nand phenylvinylsulfoxide. Full conversion but very low yields (<5%)\nwere obtained with vinyl diethylphosphonate or 5,6-dihydro-2H-pyran-2-one."},{"key":"ref29\/cit29a","volume-title":"Density Functional Theory of Atoms and Molecules","author":"Parr R. G.","year":"1989"},{"key":"ref31\/cit31","doi-asserted-by":"publisher","DOI":"10.1021\/acscentsci.8b00005"},{"key":"ref32\/cit32","unstructured":"Some studies\non Pd-catalysis\nin the presence of silver salts invoke the intervention of bimetallic\nPd\/Ag species (see next reference). However, a coupling reaction carried\nout between limonene and ethyl acrylate using a stoichiometric amount\nof Pd(OAc)2 and in the absence of AgOAc, gave the expected\nproduct 3aa in 50% isolated yield (71:29 E\/Z). This result\nsuggests that the silver salt in this coupling is only responsible\nfor the Pd(0) reoxidation step."},{"key":"ref33\/cit33a","doi-asserted-by":"publisher","DOI":"10.1039\/D3CS00328K"},{"key":"ref33\/cit33b","doi-asserted-by":"publisher","DOI":"10.1039\/D2DT03948F"},{"key":"ref33\/cit33c","doi-asserted-by":"publisher","DOI":"10.1021\/acscatal.1c02552"},{"key":"ref33\/cit33d","doi-asserted-by":"publisher","DOI":"10.1039\/C9SC04540F"},{"key":"ref33\/cit33e","doi-asserted-by":"publisher","DOI":"10.1016\/j.jorganchem.2017.12.026"},{"key":"ref33\/cit33f","doi-asserted-by":"publisher","DOI":"10.1021\/acscatal.7b02974"},{"key":"ref33\/cit33g","doi-asserted-by":"publisher","DOI":"10.1021\/ja412770h"},{"key":"ref33\/cit33h","doi-asserted-by":"publisher","DOI":"10.1021\/ja410485g"},{"key":"ref34\/cit34a","doi-asserted-by":"publisher","DOI":"10.1103\/PhysRevA.75.063204"},{"key":"ref34\/cit34b","doi-asserted-by":"publisher","DOI":"10.1103\/PhysRevA.75.033202"},{"key":"ref34\/cit34c","doi-asserted-by":"publisher","DOI":"10.1103\/PhysRevA.72.045201"},{"key":"ref34\/cit34d","doi-asserted-by":"publisher","DOI":"10.1002\/jcc.25577"},{"key":"ref35\/cit35","unstructured":"Ag octamers\n(n = 8), and octakaidecamers (n =\n18) are considered\nto become more stable than other clusters."},{"key":"ref36\/cit36","unstructured":"In truth, the energetic span\nis the difference between the energy of the transition state leading\nto Pd(THF)2, which is expected to be the turnover frequency\ndetermining transition state (TDTS) and that of the resting state.\nHowever, as the step of the release of Pd(THF)2 is highly\nendergonic, according to the Hammond postulate, it should feature\na rather late transition state, energetically and geometrically very\nsimilar to the state of Pd(THF)2."},{"key":"ref37\/cit37a","doi-asserted-by":"publisher","DOI":"10.1039\/C9CC00754G"},{"key":"ref37\/cit37b","doi-asserted-by":"publisher","DOI":"10.1002\/wcms.1372"},{"key":"ref38\/cit38","doi-asserted-by":"publisher","DOI":"10.1021\/ol300442w"},{"key":"ref39\/cit39a","doi-asserted-by":"publisher","DOI":"10.1021\/om050703v"},{"key":"ref39\/cit39b","doi-asserted-by":"publisher","DOI":"10.1038\/s44160-022-00145-x"},{"key":"ref39\/cit39c","doi-asserted-by":"publisher","DOI":"10.1055\/s-2006-948208"},{"key":"ref40\/cit40a","doi-asserted-by":"publisher","DOI":"10.3390\/molecules28124809"},{"key":"ref40\/cit40b","doi-asserted-by":"publisher","DOI":"10.1039\/C8GC00616D"},{"key":"ref41\/cit41","doi-asserted-by":"publisher","DOI":"10.1002\/cctc.201601645"},{"key":"ref42\/cit42a","doi-asserted-by":"publisher","DOI":"10.3762\/bjoc.14.61"},{"key":"ref42\/cit42b","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201705499"},{"key":"ref42\/cit42c","doi-asserted-by":"publisher","DOI":"10.1039\/D0SC06000C"},{"key":"ref43\/cit43a","doi-asserted-by":"publisher","DOI":"10.1021\/ol801471f"},{"key":"ref43\/cit43b","doi-asserted-by":"publisher","DOI":"10.1002\/hlca.201900024"},{"key":"ref43\/cit43c","unstructured":"cBraje, W.; Britze, K.; Dietrich, J. D.; Jolit, A.; Kaschel, J.; Klee, J.; Lindner, T. Organic Reactions Carried out in Aqueous Solution in the Presence of a Hydroxyalkyl(alkyl)cellulose or an Alkylcellulose. Patent 2017, WO 2017\/129796."},{"key":"ref43\/cit43d","doi-asserted-by":"publisher","DOI":"10.1016\/j.checat.2022.12.002"},{"key":"ref44\/cit44","unstructured":"The same coupling carried\nout\nunder classical conditions on a 1.0 mmol scale with the catalytic\nsystem [PdCl2(PPh3)2 (0.2 mol%),\nCuI (5 mol%), NEt3 (3.0 equiv.)] in DMF for 24 h at 45\n\u00b0C, afforded 4 in 44% isolated yield."},{"key":"ref45\/cit45","doi-asserted-by":"publisher","DOI":"10.26434\/chemrxiv-2024-nzkq1"}],"container-title":["The Journal of Organic Chemistry"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/pubs.acs.org\/doi\/pdf\/10.1021\/acs.joc.4c00501","content-type":"application\/pdf","content-version":"vor","intended-application":"unspecified"},{"URL":"https:\/\/pubs.acs.org\/doi\/pdf\/10.1021\/acs.joc.4c00501","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2024,8,2]],"date-time":"2024-08-02T10:51:56Z","timestamp":1722595916000},"score":1,"resource":{"primary":{"URL":"https:\/\/pubs.acs.org\/doi\/10.1021\/acs.joc.4c00501"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2024,7,18]]},"references-count":99,"journal-issue":{"issue":"15","published-print":{"date-parts":[[2024,8,2]]}},"alternative-id":["10.1021\/acs.joc.4c00501"],"URL":"https:\/\/doi.org\/10.1021\/acs.joc.4c00501","relation":{},"ISSN":["0022-3263","1520-6904"],"issn-type":[{"value":"0022-3263","type":"print"},{"value":"1520-6904","type":"electronic"}],"subject":[],"published":{"date-parts":[[2024,7,18]]}}}