Copper Catalyzed SP3 C-H Functionalization for C-O, C-N, and C-C Bond Formation
Abstract
C-H functionalization allows us to convert C-H bonds into a variety of functional groups. Using copper as a catalyst with tBuOO tBu as an oxidant, we have been successful in converting sp 3 C-H bonds into new C-O, C-N, and C-C bonds. Aliphatic alcohols afford dialkyl ether products using a variety of R-H substrates enabling the construction of diverse set of compounds. Overcoming the limitation that phenols don’t afford desired ether products efficiently, we are able to use acyl protected phenols to generate aryl alkyl ethers. Expanding on this approach of protecting group exchange, TMSNCO affords boc-protected amines from different R-H substrates in high yields. Triaryl and trialkyl boranes appears to be efficient transmetallating sources upon reacting with different R-H substrates to generate new sp 3 – sp3 bond or new a sp2- p 3 bond. Rarely observed in literature, our chemistry allows us to access sterically hindered R-H substrates enabling us to construct hindered species. We have also been successful in isolating key intermediates allowing us further mechanistic insight into our proposed mechanisms.
Degree
Ph.D.
Advisors
Uyeda, Purdue University.
Subject Area
Inorganic chemistry|Organic chemistry
Off-Campus Purdue Users:
To access this dissertation, please log in to our
proxy server.
