C(sp2)–H Functionalizations Employing 2-Aminophenyl-1H-pyrazole as a New Removable Directing Group

<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>

Name thesis:degree_name

Master of Science in Chemistry

Level thesis:degree_level

Thesis

Discipline thesis:degree_discipline

Chemistry

Year dc:date.available

2017

Author dc:creator

• LEE, WAN-CHEN

Contributors dc:contributor

• Jie Jack Li
• Ryan West
• Giovanni Meloni

• copper-mediated
• C–H activation
• directing group
• amidation
• chlorination
• alkynylation
• Chemistry
• Organic Chemistry

Repository record dc:identifier

https://repository.usfca.edu/thes/223

OAI identifier oai:identifier

oai:repository.usfca.edu:thes-1289