Date of Award
Master of Science (MS)
This thesis is concerned with the one-pot reactions that are considered to be beneficial to preserve resources, save time, and are deemed a green chemistry strategy. To plan such one-pot reactions, it is important to combine two or more reactions that are compatible with each other and can be run under the same reaction conditions. In this work, possibilities of a combination of Wittig-olefination and Suzuki C-C-cross coupling reactions are explored further. Reaction sequences involve the combination of a Suzuki-reaction / Wittig olefination, a Suzuki reaction / Wittig olefination/hydrolysis, and a Suzuki-reaction / double Wittig olefination. In all cases, stabilized Wittig reagents were used. Also, a novel one-pot O-alkylation / Wittig olefination of hydroxybenzaldehydes to alkoxycinnamates was developed. Furthermore, during the synthesis of starting materials a new approach to arylmaleimides was found, using a modified Appel-type reaction.
Some of the compounds that could be made by one-pot Suzuki and single Wittig olefination are methyl 3-(3’-nitrophenyl) cinnamate, methyl (E, E)-5-(4’-nitro-1,1’- biphen-4-yl)-Penta-2,5-dienoate, methyl (E,E)-5-(3’-nitrobiphenyl)Penta-2,4- dienoate. Moreover, the combination between Suzuki – Wittig olefination and hydrolysis in one pot was performed to obtain 3-(3“-nitrobiphen-3’-yl) acrylic acid. Furthermore, dimethyl biphenyl-4,4’-diacrylate and dimethyl biphenyl-3,4’-diacrylate were synthesized by one-pot Suzuki and double Wittig olefination reaction
Mohamed Ali, Areej Hashim Elamin, "ONE-POT O-ALKYLATION AND C-C CROSS-COUPLING REACTIONS INVOLVING STABILIZED PHOSPHORANES" (2020). Theses. 826.