2-Aminophenyl-1H-pyrazole (2-APP) was discovered as a novel removable bidentate directing group for copper-mediated aerobic oxidative C(sp2)–H bond amidation and sulfonamidation bearing a wide range of sulfonamides, When Cu(OAc)2 was employed as the copper source, 1,1,3,3-tetramethylguanidine (TMG) as an organic base, the reaction, optimally carried out overnight in DMSO at 80 °C in open air, produced a variety of products in moderate to excellent yields. In addition, C(sp2)–H bond chlorination has been developed by using this auxiliary, employing trichloroacetamide as a new chlorine source. Furthermore, this unprecedented directing group also can assist copper-mediated regio-selective hydroxylation, and ortho-alkynylation/annulation by using Cu(OAc)2 as an oxidant.
","abstract_html":"<p>2-Aminophenyl-1H-pyrazole (2-APP) was discovered as a novel removable bidentate directing group for copper-mediated aerobic oxidative C(sp2)–H bond amidation and sulfonamidation bearing a wide range of sulfonamides, When Cu(OAc)2 was employed as the copper source, 1,1,3,3-tetramethylguanidine (TMG) as an organic base, the reaction, optimally carried out overnight in DMSO at 80 °C in open air, produced a variety of products in moderate to excellent yields. In addition, C(sp2)–H bond chlorination has been developed by using this auxiliary, employing trichloroacetamide as a new chlorine source. Furthermore, this unprecedented directing group also can assist copper-mediated regio-selective hydroxylation, and ortho-alkynylation/annulation by using Cu(OAc)2 as an oxidant. </p>","abstract_has_math":false,"creators":["LEE, WAN-CHEN"],"institution":null,"degree_name":"Master of Science in Chemistry","degree_level":"Thesis","degree_discipline":"Chemistry","degree_department":null,"school":null,"contributors":["Jie Jack Li","Ryan West","Giovanni Meloni"],"advisors":[],"committee_chairs":[],"committee_members":[],"year":2017,"date_issued":"2017-05-18T07:00:00Z","date_published":"2017-05-18T07:00:00Z","updated_at":"2026-07-24T05:43:52Z","subjects":["copper-mediated","C–H activation","directing group","amidation","chlorination","alkynylation","Chemistry","Organic Chemistry"],"languages":[],"rights":[],"rights_urls":[],"identifier_entries":[]},"links":{"outbound_url":"https://repository.usfca.edu/thes/223","outbound_label":"Repository record","outbound_source":"dc:identifier"},"metadata_groups":[{"id":"people","label":"People","entries":[{"key":"dc:contributor","label":"Contributor","values":["Jie Jack Li","Ryan West","Giovanni Meloni"]},{"key":"dc:creator","label":"Author","values":["LEE, WAN-CHEN"]}]},{"id":"academic_context","label":"Academic Context","entries":[{"key":"dc:date.available","label":"Dc Date Available","values":["2017-05-23T07:00:00Z"]},{"key":"thesis:degree_discipline","label":"Discipline","values":["Chemistry"]},{"key":"thesis:degree_level","label":"Degree Level","values":["Thesis"]},{"key":"thesis:degree_name","label":"Degree Name","values":["Master of Science in Chemistry"]}]},{"id":"subjects_keywords","label":"Subjects and Keywords","entries":[{"key":"dc:subject","label":"Dc Subject","values":["copper-mediated","C–H activation","directing group","amidation","chlorination","alkynylation","Chemistry","Organic Chemistry"]}]},{"id":"identifiers","label":"Identifiers","entries":[{"key":"dc:identifier","label":"Identifier","values":["https://repository.usfca.edu/thes/223"]}]},{"id":"additional","label":"Additional Metadata","entries":[{"key":"dc:description.abstract","label":"Abstract","values":["2-Aminophenyl-1H-pyrazole (2-APP) was discovered as a novel removable bidentate directing group for copper-mediated aerobic oxidative C(sp2)–H bond amidation and sulfonamidation bearing a wide range of sulfonamides, When Cu(OAc)2 was employed as the copper source, 1,1,3,3-tetramethylguanidine (TMG) as an organic base, the reaction, optimally carried out overnight in DMSO at 80 °C in open air, produced a variety of products in moderate to excellent yields. In addition, C(sp2)–H bond chlorination has been developed by using this auxiliary, employing trichloroacetamide as a new chlorine source. Furthermore, this unprecedented directing group also can assist copper-mediated regio-selective hydroxylation, and ortho-alkynylation/annulation by using Cu(OAc)2 as an oxidant.
"]},{"key":"dc:title","label":"Title","values":["C(sp2)–H Functionalizations Employing 2-Aminophenyl-1H-pyrazole as a New Removable Directing Group"]}]}],"canonical_facts":{"dc:contributor":["Jie Jack Li","Ryan West","Giovanni Meloni"],"dc:creator":["LEE, WAN-CHEN"],"dc:date.available":["2017-05-23T07:00:00Z"],"dc:description.abstract":["2-Aminophenyl-1H-pyrazole (2-APP) was discovered as a novel removable bidentate directing group for copper-mediated aerobic oxidative C(sp2)–H bond amidation and sulfonamidation bearing a wide range of sulfonamides, When Cu(OAc)2 was employed as the copper source, 1,1,3,3-tetramethylguanidine (TMG) as an organic base, the reaction, optimally carried out overnight in DMSO at 80 °C in open air, produced a variety of products in moderate to excellent yields. In addition, C(sp2)–H bond chlorination has been developed by using this auxiliary, employing trichloroacetamide as a new chlorine source. Furthermore, this unprecedented directing group also can assist copper-mediated regio-selective hydroxylation, and ortho-alkynylation/annulation by using Cu(OAc)2 as an oxidant.
"],"dc:identifier":["https://repository.usfca.edu/thes/223"],"dc:subject":["copper-mediated","C–H activation","directing group","amidation","chlorination","alkynylation","Chemistry","Organic Chemistry"],"dc:title":["C(sp2)–H Functionalizations Employing 2-Aminophenyl-1H-pyrazole as a New Removable Directing Group"],"thesis:degree_discipline":["Chemistry"],"thesis:degree_level":["Thesis"],"thesis:degree_name":["Master of Science in Chemistry"]},"updated_at":"2026-07-24T05:43:52Z"}