Date of Award


Document Type

Campus Access Thesis

Degree Name

Master of Science (MS)



First Advisor

Wei Zhang

Second Advisor

Marianna Torok

Third Advisor

Jonathan Rochford


Green chemistry integrates the environmental benign and sustainable protocols for chemical research and production. Recently, many synthetic approaches with green chemistry aspects have been developed. For example, microwave irradiation applies energy directly to solvents and reactants, which significantly reduces the reaction time. Multicomponent reactions (MCRs) incorporate reactants for the rapid construction of complex molecules. Fluorous solid-phase extraction (F-SPE) is a chromatography-free purification method that reduces the amount of solvent used.

These new techniques have been applied to construct a series of heterocyclic molecules: bridged oxazabicycle, which has been found to be an example of a bicycle-based photochromic colorant and the ideal substrate to study the molecular switch; pyranopyrazole, which is considered to be an important pharmaceutical scaffold; and 1,4-dihydropyridine, which has been reported as a multi-drug resistance (MDR) reversing agent.

A combination of advanced green techniques is applied to our perfluorooctanesulfonyl benzaldehyde-based synthesis to assemble a series of heterocyclic scaffolds. Perfluorooctanesulfonyl (C8F17O2SO-) protected benzaldehyde is used as a limiting reagent for MCRs to form the condensed product. MCRs are performed under microwave irradiation to quickly assemble the heterocyclic skeleton, and microwave-assisted Suzuki-Miyaura cross-coupling reactions remove the fluorous tag and introduce biaryl functionality to the heterocyclic compounds. The intermediates are isolated from the reaction mixtures by F-SPE. Our synthetic routes demonstrate the green chemistry approaches of microwave-assisted fast reactions; high atom economic MCRs; and chromatography-free F-SPE that could significantly improve the synthetic efficiency.


Free and open access to this Campus Access Thesis is made available to the UMass Boston community by ScholarWorks at UMass Boston. Those not on campus and those without a UMass Boston campus username and password may gain access to this thesis through resources like Proquest Dissertations & Theses Global or through Interlibrary Loan. If you have a UMass Boston campus username and password and would like to download this work from off-campus, click on the "Off-Campus UMass Boston Users" link above.