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Investigation of methods to synthesize indoles using nickel catalysis

University of British Columbia

Efforts toward the development of a regioselective synthesis of functionalized indoles with nickel catalysis are reported. Unsymmetrical alkynes with various aromatic and heteroatom-containing functional groups were synthesized and reacted with substituted anilines in the presence of bis(cyclooctadiene)nickel(0) to generate two new indoles and a 2-alkenylaniline in 40 – 50% yield. The nickel-catalyzed Suzuki-Miyaura and Kumada cross-coupling methods were also explored utilizing benzoxathiazole 2-oxides and benzoxathiazole 2,2-dioxides. This methodology enabled the synthesis of six benzoxathiazoles in 33 – 55% yield as well as the isolation of a nickel-benzoxathiazole complex.

Text

2019-03-18

Attribution-NonCommercial-NoDerivatives 4.0 International

http://hdl.handle.net/2429/68904

Chemistry

University of British Columbia

UBCV

http://creativecommons.org/licenses/by-nc-nd/4.0/