{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,8,17]],"date-time":"2026-08-17T14:29:18Z","timestamp":1786976958536,"version":"build-2736575974"},"reference-count":116,"publisher":"Wiley","issue":"50","license":[{"start":{"date-parts":[[2021,11,3]],"date-time":"2021-11-03T00:00:00Z","timestamp":1635897600000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"content-domain":{"domain":["onlinelibrary.wiley.com"],"crossmark-restriction":true},"short-container-title":["Angew Chem Int Ed"],"published-print":{"date-parts":[[2021,12,6]]},"abstract":"<jats:title>Abstract<\/jats:title>\n                  <jats:p>\n                    Organophosphonium salts containing C(sp\n                    <jats:sup>3<\/jats:sup>\n                    )\u2212\n                    <jats:sup>+<\/jats:sup>\n                    P bonds are among the most utilized reagents in organic synthesis for constructing C\u2212C double bonds. However, their use as C\u2010selective electrophilic groups is rare. Here, we explore an efficient and general transition\u2010metal\u2010free method for sequential chemo\u2010 and regioselective C\u2212H and C(sp\n                    <jats:sup>3<\/jats:sup>\n                    )\u2212\n                    <jats:sup>+<\/jats:sup>\n                    P bond functionalizations. In the present study, C\u2212H alkylation resulting in the synthesis of benzhydryl triarylphosphonium salts was achieved by one\u2010pot, four\u2010component cross\u2010coupling reactions of simple and commercially available starting materials. The utility of the resulting phosphonium salt building blocks was demonstrated by the chemoselective post\u2010functionalization of benzylic C(sp\n                    <jats:sup>3<\/jats:sup>\n                    )\u2212\n                    <jats:sup>+<\/jats:sup>\n                    PPh\n                    <jats:sub>3<\/jats:sub>\n                    groups to achieve aminations, thiolations, and arylations. In this way, benzhydrylamines, benzhydrylthioethers, and triarylmethanes, structural motifs that are present in many pharmaceuticals and agrochemicals, are readily accessed. These include the synthesis of two anticancer agents from simple materials in only two to three steps. Additionally, a protocol for late\u2010stage functionalization of bioactive drugs has been developed using benzhydrylphosphonium salts. This new approach should provide novel transformations for application in both academic and pharmaceutical research.\n                  <\/jats:p>","DOI":"10.1002\/anie.202111164","type":"journal-article","created":{"date-parts":[[2021,10,8]],"date-time":"2021-10-08T21:00:57Z","timestamp":1633726857000},"page":"26199-26209","update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":41,"title":["Sequential Selective C\u2212H and C(sp\n                    <sup>3<\/sup>\n                    )\u2212\n                    <sup>+<\/sup>\n                    P Bond Functionalizations: An Entry to Bioactive Arylated Scaffolds"],"prefix":"10.1002","volume":"60","author":[{"ORCID":"https:\/\/orcid.org\/0000-0003-1063-2952","authenticated-orcid":false,"given":"K. Naresh","family":"Babu","sequence":"first","affiliation":[{"name":"Institute of Chemistry The Hebrew University of Jerusalem  Jerusalem 9190401 Israel"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Fedaa","family":"Massarwe","sequence":"additional","affiliation":[{"name":"Institute of Chemistry The Hebrew University of Jerusalem  Jerusalem 9190401 Israel"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Israa","family":"Shioukhi","sequence":"additional","affiliation":[{"name":"Institute of Chemistry The Hebrew University of Jerusalem  Jerusalem 9190401 Israel"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-6992-5595","authenticated-orcid":false,"given":"Ahmad","family":"Masarwa","sequence":"additional","affiliation":[{"name":"Institute of Chemistry The Hebrew University of Jerusalem  Jerusalem 9190401 Israel"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2021,11,3]]},"reference":[{"key":"e_1_2_6_1_1","unstructured":"\u00a0"},{"key":"e_1_2_6_2_2","doi-asserted-by":"publisher","DOI":"10.1126\/science.1114731"},{"key":"e_1_2_6_3_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.199104553"},{"key":"e_1_2_6_3_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.19911030504"},{"key":"e_1_2_6_4_1","unstructured":"\u00a0"},{"key":"e_1_2_6_5_2","doi-asserted-by":"publisher","DOI":"10.1038\/nchem.1607"},{"key":"e_1_2_6_6_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202011901"},{"key":"e_1_2_6_6_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.202011901"},{"key":"e_1_2_6_7_1","doi-asserted-by":"publisher","DOI":"10.1126\/science.aas8961"},{"key":"e_1_2_6_8_1","unstructured":"\u00a0"},{"key":"e_1_2_6_9_2","doi-asserted-by":"publisher","DOI":"10.1039\/D0SC03833D"},{"key":"e_1_2_6_10_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.0c04674"},{"key":"e_1_2_6_11_1","unstructured":"\u00a0"},{"key":"e_1_2_6_12_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.8b04530"},{"key":"e_1_2_6_13_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201704948"},{"key":"e_1_2_6_13_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201704948"},{"key":"e_1_2_6_14_1","unstructured":"\u00a0"},{"key":"e_1_2_6_15_2","doi-asserted-by":"publisher","DOI":"10.1039\/C6GC01630H"},{"key":"e_1_2_6_16_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.chemrev.8b00081"},{"key":"e_1_2_6_17_1","unstructured":"\u00a0"},{"key":"e_1_2_6_18_2","doi-asserted-by":"publisher","DOI":"10.1246\/cl.1989.1397"},{"key":"e_1_2_6_19_2","doi-asserted-by":"publisher","DOI":"10.1021\/jm0491849"},{"key":"e_1_2_6_20_2","doi-asserted-by":"publisher","DOI":"10.1039\/a902437i"},{"key":"e_1_2_6_21_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4039(00)73857-3"},{"key":"e_1_2_6_22_2","doi-asserted-by":"publisher","DOI":"10.1055\/s-1995-5186"},{"key":"e_1_2_6_23_2","doi-asserted-by":"publisher","DOI":"10.1039\/c39850000672"},{"key":"e_1_2_6_24_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.tet.2006.03.109"},{"key":"e_1_2_6_25_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4020(01)00558-0"},{"key":"e_1_2_6_26_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr068357u"},{"key":"e_1_2_6_27_2","doi-asserted-by":"publisher","DOI":"10.5012\/bkcs.2006.27.5.744"},{"key":"e_1_2_6_28_1","unstructured":"\u00a0"},{"key":"e_1_2_6_29_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4020(98)00899-0"},{"key":"e_1_2_6_30_2","doi-asserted-by":"publisher","DOI":"10.1002\/ejoc.200800070"},{"key":"e_1_2_6_31_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200804140"},{"key":"e_1_2_6_31_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.200804140"},{"key":"e_1_2_6_32_1","doi-asserted-by":"publisher","DOI":"10.1002\/adsc.200606138"},{"key":"e_1_2_6_33_1","unstructured":"\u00a0"},{"key":"e_1_2_6_34_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.197704233"},{"key":"e_1_2_6_34_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.19770890704"},{"key":"e_1_2_6_35_2","doi-asserted-by":"publisher","DOI":"10.1039\/c3cs60105f"},{"key":"e_1_2_6_36_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr00094a007"},{"key":"e_1_2_6_37_2","doi-asserted-by":"publisher","DOI":"10.1002\/slct.202002192"},{"key":"e_1_2_6_38_1","unstructured":"\u00a0"},{"key":"e_1_2_6_39_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.6b08662"},{"key":"e_1_2_6_40_2","doi-asserted-by":"publisher","DOI":"10.1055\/s-0036-1591850"},{"key":"e_1_2_6_41_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.tet.2017.12.040"},{"key":"e_1_2_6_42_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.0c00882"},{"key":"e_1_2_6_43_1","unstructured":"\u00a0"},{"key":"e_1_2_6_44_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr00104a004"},{"key":"e_1_2_6_45_2","doi-asserted-by":"publisher","DOI":"10.1021\/ic00258a033"},{"key":"e_1_2_6_46_2","doi-asserted-by":"publisher","DOI":"10.1021\/j100328a018"},{"key":"e_1_2_6_47_2","doi-asserted-by":"publisher","DOI":"10.1021\/cm103548t"},{"key":"e_1_2_6_48_2","doi-asserted-by":"publisher","DOI":"10.1039\/C8CC02173B"},{"key":"e_1_2_6_49_1","unstructured":"\u00a0"},{"key":"e_1_2_6_50_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja511639b"},{"key":"e_1_2_6_51_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.tet.2015.05.055"},{"key":"e_1_2_6_52_2","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201404500"},{"key":"e_1_2_6_53_2","doi-asserted-by":"publisher","DOI":"10.1002\/ejoc.201001700"},{"key":"e_1_2_6_54_2","doi-asserted-by":"publisher","DOI":"10.1021\/ar020094c"},{"key":"e_1_2_6_55_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja306522b"},{"key":"e_1_2_6_56_2","doi-asserted-by":"publisher","DOI":"10.1021\/ar100091m"},{"key":"e_1_2_6_57_2","doi-asserted-by":"publisher","DOI":"10.1002\/chem.202100977"},{"key":"e_1_2_6_58_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja3017522"},{"key":"e_1_2_6_59_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201916449"},{"key":"e_1_2_6_59_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201916449"},{"key":"e_1_2_6_60_1","unstructured":"\u00a0"},{"key":"e_1_2_6_61_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201700945"},{"key":"e_1_2_6_61_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201700945"},{"key":"e_1_2_6_62_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.joc.1c00285"},{"key":"e_1_2_6_63_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo00296a020"},{"key":"e_1_2_6_64_1","doi-asserted-by":"publisher","DOI":"10.1016\/0960-0760(90)90460-3"},{"key":"e_1_2_6_65_1","doi-asserted-by":"publisher","DOI":"10.1002\/ejoc.201801888"},{"key":"e_1_2_6_66_1","doi-asserted-by":"publisher","DOI":"10.2174\/1570178615666180110161450"},{"key":"e_1_2_6_67_1","unstructured":"\u00a0"},{"key":"e_1_2_6_68_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.7b12212"},{"key":"e_1_2_6_69_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.9b02990"},{"key":"e_1_2_6_70_2","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201805638"},{"key":"e_1_2_6_71_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.8b02196"},{"key":"e_1_2_6_72_1","unstructured":"\u00a0"},{"key":"e_1_2_6_73_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201913069"},{"key":"e_1_2_6_73_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201913069"},{"key":"e_1_2_6_74_2","doi-asserted-by":"publisher","DOI":"10.1039\/D0OB01989E"},{"key":"e_1_2_6_75_1","unstructured":"\u00a0"},{"key":"e_1_2_6_76_2","doi-asserted-by":"publisher","DOI":"10.1001\/jama.1983.03330350053028"},{"key":"e_1_2_6_77_2","first-page":"1199","volume":"105","author":"Thorlacius K.","year":"2008","journal-title":"Laekartidningen"},{"key":"e_1_2_6_78_2","doi-asserted-by":"publisher","DOI":"10.1111\/j.1365-2125.1978.tb04588.x"},{"key":"e_1_2_6_79_1","unstructured":"\u00a0"},{"key":"e_1_2_6_80_2","doi-asserted-by":"publisher","DOI":"10.1021\/acscentsci.9b00916"},{"key":"e_1_2_6_81_2","doi-asserted-by":"publisher","DOI":"10.1080\/17460441.2019.1653850"},{"key":"e_1_2_6_82_2","first-page":"5493","volume":"6","author":"He J.","year":"2015","journal-title":"Nat. Commun."},{"key":"e_1_2_6_83_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.8b00813"},{"key":"e_1_2_6_84_1","unstructured":"\u00a0"},{"key":"e_1_2_6_85_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.chemrev.9b00665"},{"key":"e_1_2_6_86_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4020(01)92229-X"},{"key":"e_1_2_6_87_1","unstructured":"\u00a0"},{"key":"e_1_2_6_88_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.euroneuro.2015.07.028"},{"key":"e_1_2_6_89_2","doi-asserted-by":"publisher","DOI":"10.1185\/030079904125004457"},{"key":"e_1_2_6_90_1","unstructured":"\u00a0"},{"key":"e_1_2_6_91_2","doi-asserted-by":"publisher","DOI":"10.1002\/ejoc.201900465"},{"key":"e_1_2_6_92_2","doi-asserted-by":"publisher","DOI":"10.1021\/acscatal.5b00909"},{"key":"e_1_2_6_93_2","doi-asserted-by":"publisher","DOI":"10.1093\/pcp\/pcw140"},{"key":"e_1_2_6_94_1","unstructured":"\u00a0"},{"key":"e_1_2_6_95_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.bmcl.2007.10.083"},{"key":"e_1_2_6_96_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.bmc.2005.10.002"},{"key":"e_1_2_6_97_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202102192"},{"key":"e_1_2_6_97_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.202102192"},{"key":"e_1_2_6_98_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja412159g"},{"key":"e_1_2_6_99_1","unstructured":"\u00a0"},{"key":"e_1_2_6_100_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202101682"},{"key":"e_1_2_6_100_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.202101682"},{"key":"e_1_2_6_101_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201307019"},{"key":"e_1_2_6_101_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201307019"},{"key":"e_1_2_6_102_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.5b03277"},{"key":"e_1_2_6_103_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.tetlet.2015.02.121"},{"key":"e_1_2_6_104_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.joc.8b01428"},{"key":"e_1_2_6_105_1","unstructured":"Deposition numbers\u20052085999(1\u2009b) 2085998 (1\u2009u) 2085987 (1\u2009ab) 2085997 (5\u2009s) 2085988 (10\u2009k) 2085986 (11\u2009g) 2085984 (11\u2009i) 2085985 (11\u2009o) and 2105565 (1\u2009n-C-S) contain the supplementary crystallographic data for this paper. These data are provided free of charge by the joint Cambridge Crystallographic Data Centre and Fachinformationszentrum KarlsruheAccess Structures service."}],"container-title":["Angewandte Chemie International Edition"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/anie.202111164","content-type":"application\/pdf","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/full-xml\/10.1002\/anie.202111164","content-type":"application\/xml","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/anie.202111164","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2023,8,28]],"date-time":"2023-08-28T01:34:32Z","timestamp":1693186472000},"score":1,"resource":{"primary":{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/10.1002\/anie.202111164"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2021,11,3]]},"references-count":116,"journal-issue":{"issue":"50","published-print":{"date-parts":[[2021,12,6]]}},"alternative-id":["10.1002\/anie.202111164"],"URL":"https:\/\/doi.org\/10.1002\/anie.202111164","archive":["Portico"],"relation":{},"ISSN":["1433-7851","1521-3773"],"issn-type":[{"value":"1433-7851","type":"print"},{"value":"1521-3773","type":"electronic"}],"subject":[],"published":{"date-parts":[[2021,11,3]]},"assertion":[{"value":"2021-08-18","order":0,"name":"received","label":"Received","group":{"name":"publication_history","label":"Publication History"}},{"value":"2021-11-03","order":2,"name":"published","label":"Published","group":{"name":"publication_history","label":"Publication History"}}]}}