{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,3,11]],"date-time":"2026-03-11T03:12:56Z","timestamp":1773198776806,"version":"3.50.1"},"reference-count":159,"publisher":"Wiley","issue":"16","license":[{"start":{"date-parts":[[2018,7,4]],"date-time":"2018-07-04T00:00:00Z","timestamp":1530662400000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"funder":[{"name":"Funda\u00e7\u00e3o para a Ci\u00eancia e a Tecnologia","award":["UID\/QUI\/00100\/2013"],"award-info":[{"award-number":["UID\/QUI\/00100\/2013"]}]}],"content-domain":{"domain":["chemistry-europe.onlinelibrary.wiley.com"],"crossmark-restriction":true},"short-container-title":["ChemCatChem"],"published-print":{"date-parts":[[2018,8,21]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p>Cross\u2010dehydrogenative coupling of two C\u2212H bonds or a C\u2212H and an X\u2212H bond (X=N, O, P, S, etc.) has emerged as a powerful new synthetic methodology in the last 12\u2005years. Using this approach, simple ethers, often utilized as solvents, and more complex ones, as well as thioethers, have become important alkylating agents, when reacted directly, under oxidative conditions in the presence of suitable reagents. This environmentally friendly, sustainable procedure, has been used to alkylate a wide range of substrates, from simple ketones and acids to alkyl benzenes, coumarins, indoles, oxazoles, benzoxazoles or (benzo)thiazoles and more. This Review is a systematic presentation of the developments in transition metal\u2010catalyzed CDC reactions, including photoredox processes, which took place between 2014 and early 2018, with an emphasis on the later years.<\/jats:p>","DOI":"10.1002\/cctc.201800582","type":"journal-article","created":{"date-parts":[[2018,6,15]],"date-time":"2018-06-15T05:55:25Z","timestamp":1529042125000},"page":"3354-3383","update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":94,"title":["Recent Developments in Transition Metal\u2010Catalyzed Cross\u2010Dehydrogenative Coupling Reactions of Ethers and Thioethers"],"prefix":"10.1002","volume":"10","author":[{"ORCID":"https:\/\/orcid.org\/0000-0002-3101-016X","authenticated-orcid":false,"given":"Ana Maria","family":"Faisca\u2005Phillips","sequence":"first","affiliation":[{"name":"Centro de Qu\u00edmica Estrutural Complexo I Instituto Superior T\u00e9cnico Universidade de Lisboa  Av. Rovisco Pais 1049-001 Lisboa Portugal"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-8323-888X","authenticated-orcid":false,"given":"Armando J. L.","family":"Pombeiro","sequence":"additional","affiliation":[{"name":"Centro de Qu\u00edmica Estrutural Complexo I Instituto Superior T\u00e9cnico Universidade de Lisboa  Av. Rovisco Pais 1049-001 Lisboa Portugal"}]}],"member":"311","published-online":{"date-parts":[[2018,7,4]]},"reference":[{"key":"e_1_2_10_1_1","unstructured":"Recent reviews on C\u2212H activation:"},{"key":"e_1_2_10_2_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.molcata.2016.06.020"},{"key":"e_1_2_10_3_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.joc.5b02818"},{"key":"e_1_2_10_4_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr500431s"},{"key":"e_1_2_10_5_2","doi-asserted-by":"publisher","DOI":"10.1038\/nchem.2031"},{"key":"e_1_2_10_6_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr100280d"},{"key":"e_1_2_10_7_1","doi-asserted-by":"publisher","DOI":"10.1039\/c1cs15129k"},{"key":"e_1_2_10_8_1","doi-asserted-by":"publisher","DOI":"10.1021\/cr800541y"},{"key":"e_1_2_10_9_1","unstructured":"Recent reviews on CDC in general:"},{"key":"e_1_2_10_10_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.tetlet.2017.01.035"},{"key":"e_1_2_10_11_2","doi-asserted-by":"publisher","DOI":"10.1021\/ar800164n"},{"key":"e_1_2_10_12_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja0390303"},{"key":"e_1_2_10_13_1","doi-asserted-by":"publisher","DOI":"10.1016\/0040-4020(95)01056-4"},{"key":"e_1_2_10_14_1","unstructured":"Recent reviews on CDC reactions of ethers:"},{"key":"e_1_2_10_15_2","doi-asserted-by":"publisher","DOI":"10.1002\/ejoc.201700341"},{"key":"e_1_2_10_16_2","doi-asserted-by":"publisher","DOI":"10.1039\/C7SC01045A"},{"key":"e_1_2_10_17_2","doi-asserted-by":"publisher","DOI":"10.1002\/adsc.201600467"},{"key":"e_1_2_10_18_1","unstructured":"\u00a0"},{"key":"e_1_2_10_19_2","doi-asserted-by":"publisher","DOI":"10.1039\/9781788010658-00193"},{"key":"e_1_2_10_20_2","first-page":"162513","author":"Rutkowski J.","year":"2013","journal-title":"BioMed Res. Int."},{"key":"e_1_2_10_21_2","doi-asserted-by":"publisher","DOI":"10.1055\/s-0033-1340073"},{"key":"e_1_2_10_22_2","doi-asserted-by":"publisher","DOI":"10.1002\/9783527800315.ch8"},{"key":"e_1_2_10_23_2","first-page":"269","volume-title":"Analogue-Based Drug Discovery","author":"B\u00f8ges\u00f8 K. P.","year":"2013"},{"key":"e_1_2_10_24_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200503255"},{"key":"e_1_2_10_24_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.200503255"},{"key":"e_1_2_10_25_1","first-page":"138","volume":"1","author":"Yoo W.-J.","year":"2009","journal-title":"Synlett"},{"key":"e_1_2_10_26_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.tet.2013.07.085"},{"key":"e_1_2_10_27_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201206610"},{"key":"e_1_2_10_27_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201206610"},{"key":"e_1_2_10_28_1","first-page":"3504","volume":"20","author":"Huang L.","year":"2009","journal-title":"Synthesis"},{"key":"e_1_2_10_29_1","doi-asserted-by":"publisher","DOI":"10.1021\/jo2021373"},{"key":"e_1_2_10_30_1","doi-asserted-by":"publisher","DOI":"10.1039\/c2sc20712e"},{"key":"e_1_2_10_31_1","doi-asserted-by":"publisher","DOI":"10.1021\/ol4022113"},{"key":"e_1_2_10_32_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.tet.2012.11.020"},{"key":"e_1_2_10_33_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.tet.2014.03.074"},{"key":"e_1_2_10_34_1","doi-asserted-by":"publisher","DOI":"10.1002\/adsc.201301091"},{"key":"e_1_2_10_35_1","doi-asserted-by":"publisher","DOI":"10.1039\/C5CC01287B"},{"key":"e_1_2_10_36_1","doi-asserted-by":"publisher","DOI":"10.1039\/C5RA27899F"},{"key":"e_1_2_10_37_1","first-page":"211","author":"He H.-F.","year":"2013","journal-title":"Synlett"},{"key":"e_1_2_10_38_1","doi-asserted-by":"publisher","DOI":"10.1039\/C6RA14697J"},{"key":"e_1_2_10_39_1","unstructured":"See for example"},{"key":"e_1_2_10_40_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0960-894X(03)00713-3"},{"key":"e_1_2_10_41_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201101391"},{"key":"e_1_2_10_41_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201101391"},{"key":"e_1_2_10_42_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja505136j"},{"key":"e_1_2_10_43_1","doi-asserted-by":"publisher","DOI":"10.1039\/C7OB02249B"},{"key":"e_1_2_10_44_1","doi-asserted-by":"publisher","DOI":"10.1021\/jo500192h"},{"key":"e_1_2_10_45_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.tetlet.2015.03.068"},{"key":"e_1_2_10_46_1","doi-asserted-by":"publisher","DOI":"10.1039\/C6NJ03876J"},{"key":"e_1_2_10_47_1","doi-asserted-by":"publisher","DOI":"10.1021\/ol5011906"},{"key":"e_1_2_10_48_1","doi-asserted-by":"publisher","DOI":"10.1002\/adsc.201500048"},{"key":"e_1_2_10_49_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.joc.5b01990"},{"key":"e_1_2_10_50_1","first-page":"10","author":"Yue Q.","year":"2018","journal-title":"Adv. Synth. Catal."},{"key":"e_1_2_10_51_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.tet.2015.03.085"},{"key":"e_1_2_10_52_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.jorganchem.2015.10.010"},{"key":"e_1_2_10_53_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.5b02217"},{"key":"e_1_2_10_54_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.tet.2016.10.014"},{"key":"e_1_2_10_55_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.joc.5b02503"},{"key":"e_1_2_10_56_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.joc.5b00800"},{"key":"e_1_2_10_57_1","unstructured":"\u00a0"},{"key":"e_1_2_10_58_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.ejmech.2014.07.013"},{"key":"e_1_2_10_59_2","doi-asserted-by":"publisher","DOI":"10.1007\/s11418-008-0246-z"},{"key":"e_1_2_10_60_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.tet.2015.07.052"},{"key":"e_1_2_10_61_1","unstructured":"For selected reviews see for example:"},{"key":"e_1_2_10_62_2","doi-asserted-by":"publisher","DOI":"10.2174\/1389557516666160801094919"},{"key":"e_1_2_10_63_2","first-page":"236","volume":"2","author":"Jain P. K.","year":"2012","journal-title":"J. Appl. Pharm. Sci."},{"key":"e_1_2_10_64_1","doi-asserted-by":"publisher","DOI":"10.1039\/c4cc00867g"},{"key":"e_1_2_10_65_1","doi-asserted-by":"publisher","DOI":"10.1039\/C4OB02564D"},{"key":"e_1_2_10_66_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.joc.6b02145"},{"key":"e_1_2_10_67_1","unstructured":"For selected reviews see"},{"key":"e_1_2_10_68_2","doi-asserted-by":"publisher","DOI":"10.1039\/C7OB00405B"},{"key":"e_1_2_10_69_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr400291c"},{"key":"e_1_2_10_70_2","doi-asserted-by":"crossref","first-page":"415","DOI":"10.1007\/0-306-46912-X_11","volume-title":"Organic Photochromic and Thermochromic Compounds, Vol. 2","author":"Samat A.","year":"2002"},{"key":"e_1_2_10_71_1","doi-asserted-by":"publisher","DOI":"10.1039\/c4qo00006d"},{"key":"e_1_2_10_72_1","doi-asserted-by":"publisher","DOI":"10.1002\/ange.200802215"},{"key":"e_1_2_10_72_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200802215"},{"key":"e_1_2_10_73_1","doi-asserted-by":"publisher","DOI":"10.1007\/s41061-016-0038-y"},{"key":"e_1_2_10_74_2","volume-title":"Ni- and Fe-based cross-coupling reactions","author":"Correa A.","year":"2016"},{"key":"e_1_2_10_75_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr500425u"},{"key":"e_1_2_10_76_1","doi-asserted-by":"publisher","DOI":"10.1021\/jo902093p"},{"key":"e_1_2_10_77_1","doi-asserted-by":"publisher","DOI":"10.1021\/ol100670m"},{"key":"e_1_2_10_78_1","doi-asserted-by":"publisher","DOI":"10.1002\/cjoc.201200690"},{"key":"e_1_2_10_79_1","doi-asserted-by":"publisher","DOI":"10.1007\/s11426-011-4435-3"},{"key":"e_1_2_10_80_1","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201210029"},{"key":"e_1_2_10_81_1","doi-asserted-by":"publisher","DOI":"10.1039\/c0cc02491k"},{"key":"e_1_2_10_82_1","doi-asserted-by":"publisher","DOI":"10.1055\/s-0033-1339683"},{"key":"e_1_2_10_83_1","first-page":"2803","volume":"17","author":"Xie Y.","year":"2011","journal-title":"Synthesis"},{"key":"e_1_2_10_84_1","doi-asserted-by":"publisher","DOI":"10.1002\/adsc.201200410"},{"key":"e_1_2_10_85_1","doi-asserted-by":"publisher","DOI":"10.1039\/C5CC05005G"},{"key":"e_1_2_10_86_1","doi-asserted-by":"publisher","DOI":"10.1021\/ol201779n"},{"key":"e_1_2_10_87_1","unstructured":"For selected reviews see for example"},{"key":"e_1_2_10_88_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.ejmech.2017.12.044"},{"key":"e_1_2_10_89_2","volume-title":"The Chemistry of Heterocycles","author":"Eicher T.","year":"2013"},{"key":"e_1_2_10_90_2","first-page":"2975","volume":"4","author":"Tomer I.","year":"2011","journal-title":"J. Pharm. Res."},{"key":"e_1_2_10_91_2","doi-asserted-by":"publisher","DOI":"10.1111\/j.1470-9465.2004.00841.x"},{"key":"e_1_2_10_92_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.tetlet.2015.06.091"},{"key":"e_1_2_10_93_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200806063"},{"key":"e_1_2_10_94_1","doi-asserted-by":"publisher","DOI":"10.1039\/C8RA00872H"},{"key":"e_1_2_10_95_1","doi-asserted-by":"publisher","DOI":"10.1039\/C7CC07235J"},{"key":"e_1_2_10_96_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.5b02504"},{"key":"e_1_2_10_97_1","doi-asserted-by":"publisher","DOI":"10.1021\/ol5004115"},{"key":"e_1_2_10_98_1","unstructured":"\u00a0"},{"key":"e_1_2_10_99_2","doi-asserted-by":"publisher","DOI":"10.1039\/a701102d"},{"key":"e_1_2_10_100_2","first-page":"370","volume-title":"Protective Groups in Organic Synthesis","author":"Greene T. W.","year":"2007"},{"key":"e_1_2_10_101_1","doi-asserted-by":"publisher","DOI":"10.1021\/acscatal.5b02344"},{"key":"e_1_2_10_102_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.7b02567"},{"key":"e_1_2_10_103_1","doi-asserted-by":"publisher","DOI":"10.1007\/s00253-003-1274-y"},{"key":"e_1_2_10_104_1","doi-asserted-by":"publisher","DOI":"10.1002\/adsc.201600349"},{"key":"e_1_2_10_105_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.joc.6b02211"},{"key":"e_1_2_10_106_1","volume-title":"Comprehensive Heterocyclic Chemistry III, Vol. 4","author":"Yeh V.","year":"2008"},{"key":"e_1_2_10_107_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201005922"},{"key":"e_1_2_10_107_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201005922"},{"key":"e_1_2_10_108_1","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201000489"},{"key":"e_1_2_10_109_1","doi-asserted-by":"publisher","DOI":"10.1002\/asia.201701258"},{"key":"e_1_2_10_110_1","unstructured":"See for example"},{"key":"e_1_2_10_111_2","doi-asserted-by":"publisher","DOI":"10.1126\/science.aad7893"},{"key":"e_1_2_10_112_2","doi-asserted-by":"publisher","DOI":"10.1039\/C4QO00068D"},{"key":"e_1_2_10_113_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.7b02316"},{"key":"e_1_2_10_114_1","unstructured":"\u00a0"},{"key":"e_1_2_10_115_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja101909t"},{"key":"e_1_2_10_116_2","doi-asserted-by":"publisher","DOI":"10.1002\/asia.201300990"},{"key":"e_1_2_10_117_1","doi-asserted-by":"publisher","DOI":"10.1002\/adsc.201400295"},{"key":"e_1_2_10_118_1","unstructured":"\u00a0"},{"key":"e_1_2_10_119_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.ejmech.2016.07.057"},{"key":"e_1_2_10_120_2","doi-asserted-by":"publisher","DOI":"10.1021\/acscatal.5b00026"},{"key":"e_1_2_10_121_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr500075s"},{"key":"e_1_2_10_122_1","doi-asserted-by":"publisher","DOI":"10.1039\/C5OB00277J"},{"key":"e_1_2_10_123_1","doi-asserted-by":"publisher","DOI":"10.1021\/acscatal.5b00026"},{"key":"e_1_2_10_124_1","doi-asserted-by":"publisher","DOI":"10.1055\/s-0034-1380694"},{"key":"e_1_2_10_125_1","doi-asserted-by":"publisher","DOI":"10.1021\/ol501485f"},{"key":"e_1_2_10_126_1","doi-asserted-by":"publisher","DOI":"10.1055\/s-0035-1560180"},{"key":"e_1_2_10_127_1","doi-asserted-by":"publisher","DOI":"10.1021\/acscatal.5b02603"},{"key":"e_1_2_10_128_1","unstructured":"\u00a0"},{"key":"e_1_2_10_129_2","doi-asserted-by":"publisher","DOI":"10.1039\/C4CC05758A"},{"key":"e_1_2_10_130_1","doi-asserted-by":"publisher","DOI":"10.1021\/jo502477r"},{"key":"e_1_2_10_131_1","unstructured":"\u00a0"},{"key":"e_1_2_10_132_2","doi-asserted-by":"publisher","DOI":"10.1002\/ejoc.201601485"},{"key":"e_1_2_10_133_2","doi-asserted-by":"publisher","DOI":"10.1002\/ejoc.201601479"},{"key":"e_1_2_10_134_2","doi-asserted-by":"publisher","DOI":"10.1002\/ejoc.201601626"},{"key":"e_1_2_10_135_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.chemrev.6b00057"},{"key":"e_1_2_10_136_2","first-page":"714","volume":"27","author":"Roth H. G.","year":"2016","journal-title":"Synlett"},{"key":"e_1_2_10_137_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.accounts.6b00275"},{"key":"e_1_2_10_138_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.joc.6b01449"},{"key":"e_1_2_10_139_2","doi-asserted-by":"publisher","DOI":"10.1039\/C4QI00053F"},{"key":"e_1_2_10_140_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja411596q"},{"key":"e_1_2_10_141_1","doi-asserted-by":"publisher","DOI":"10.1039\/a804291h"},{"key":"e_1_2_10_142_1","unstructured":"\u00a0"},{"key":"e_1_2_10_143_2","volume-title":"An Introduction to Medicinal Chemistry","author":"Patrick G. L.","year":"2009"},{"key":"e_1_2_10_144_1","volume-title":"Drug Selectivity: An Evolving Concept in Medicinal Chemistry, Vol. 72","author":"Marek G. J.","year":"2018"},{"key":"e_1_2_10_145_1","volume-title":"Principles of Organic Medicinal Chemistry","author":"Nadendla R. R.","year":"2005"},{"key":"e_1_2_10_146_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja5102695"},{"key":"e_1_2_10_147_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201410432"},{"key":"e_1_2_10_147_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201410432"},{"key":"e_1_2_10_148_1","doi-asserted-by":"publisher","DOI":"10.1039\/C5CY02290H"},{"key":"e_1_2_10_149_1","doi-asserted-by":"publisher","DOI":"10.1038\/nature19811"},{"key":"e_1_2_10_150_1","unstructured":"\u00a0"},{"key":"e_1_2_10_151_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja00132a008"},{"key":"e_1_2_10_152_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja00022a029"},{"key":"e_1_2_10_153_1","doi-asserted-by":"publisher","DOI":"10.1039\/C6CC09725A"}],"container-title":["ChemCatChem"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/api.wiley.com\/onlinelibrary\/tdm\/v1\/articles\/10.1002%2Fcctc.201800582","content-type":"application\/pdf","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/cctc.201800582","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,12]],"date-time":"2025-10-12T18:47:39Z","timestamp":1760294859000},"score":1,"resource":{"primary":{"URL":"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/10.1002\/cctc.201800582"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2018,7,4]]},"references-count":159,"journal-issue":{"issue":"16","published-print":{"date-parts":[[2018,8,21]]}},"alternative-id":["10.1002\/cctc.201800582"],"URL":"https:\/\/doi.org\/10.1002\/cctc.201800582","archive":["Portico"],"relation":{},"ISSN":["1867-3880","1867-3899"],"issn-type":[{"value":"1867-3880","type":"print"},{"value":"1867-3899","type":"electronic"}],"subject":[],"published":{"date-parts":[[2018,7,4]]},"assertion":[{"value":"2018-04-06","order":0,"name":"received","label":"Received","group":{"name":"publication_history","label":"Publication History"}},{"value":"2018-07-04","order":3,"name":"published","label":"Published","group":{"name":"publication_history","label":"Publication History"}}]}}