Our group devotes special attention to the synthesis of organofluorine compounds for medicinal applications, organophosphorus chemistry (through P(III/V) mediated/catalyzed processes), SO2 utilization and organosulfur chemistry, carboxylic acid and C–O bond activation protocols. All these areas with a particular aim to the develop catalytic processes.

In addition to organocatalyzed reactions, the PowerCat lab focuses on developing new synthetic transformations by combining the above-mentioned areas with the catalytic power of first-row earth-abundant metals such as Cu, Ni, Co, Fe as well as other valuable transition metal catalysts, either in conventional thermal processes or photoinduced/photoredox processes.

Image: Reaction setup using the new Kessil PRL160L LED lamps. Thanks to @KessilPR for their support.

Our main research areas are:
(i) Organofluorine Chemistry: New Reactions and Reagents
(ii) Utilization of carboxylic acids as abundant chemical feedstocks in catalytic synthetic transformations
(iii) Utilization of sulfur dioxide (SO2) or chemical surrogates in organometallic catalysis and synthesis.

Development of asymmetric transformations in all the three areas mentioned above stands as a critical unmet need in the field, and special attention is also devoted to this goal. Our group strives to make significant contributions that address the current limitations in those fields. Toward this goal, we continuously utilize of concepts of physical organic chemistry and computations to gain mechanistic insights that facilitate and guide the reaction discovery process. Our ultimate goal is to enable the synthetic community and expand the synthetic chemist’s toolbox. A brief description of the current projects in the group is given below.

Organofluorine Chemistry

New Reactions and Methodology: Fluorination and Fluoroalkylation

Installation of fluorine or fluoroalkyl (—RF) groups into organic molecules imparts exceedingly important and unique biological properties. Accordingly, organofluorine compounds are known to exhibit superior metabolic stability, binding affinity, membrane permeability, and enhanced pharmacokinetic profiles in some instances. Consequently, more than 20% of newly approved pharmaceuticals and approximately 40% of registered agrochemicals possess one or more fluorine atoms.

Our group focuses on developing new, efficient, and selective ways to forge C—F bonds, as well as designing new methods and reagents to perform effective C—RF bond formation, (RF = CF3, CF2H, CH2F, CF2Me, etc.) Our reagent design is guided and inspired by sustainability principles; thus, we always consider the fluorine atom supply chain. Accordingly, we strive to design recyclable fluoroalkylation (RF-transfer) reagents avoiding Ozone-Depleting Substances (ODS) in their preparation.

Expanding the Frontiers of Utilization of Carboxylic Acids and Alcohols in Catalytic Synthetic Transformations

Carboxylic acids (RCOOH) and their derivatives (acyl halides, anhydrides, esters, amides) are amongst the most common functionalities encountered in organic chemistry. Due to the multiple reaction pathways available, many different product classes have become accessible from this type of functionalities. Classical uses involve the utilization of their activated derivatives (acyl halides, anhydrides or esters) in acylation chemistry.

However, transition-metal catalysis can enable distinct reactivities (i.e. acylative, decarboxylative (-CO2) and decarbonylative (-CO) cross-couplings). Thus, the direct use of RCOOH as substrates in catalytic processes is highly desirable because of their vast structural variety, commercial availability, synthetic availability (great number of preparative methods), physicochemical properties related to storage and handling, and their vast abundance in naturally occurring compounds.

In addition to the direct utilization of carboxylic acids in acylative cross-coupling reactions, our group focuses on the development of catalytic transformations proceeding via decarbonylation (-CO) or decarboxylation (-CO2), thereby effectively and directly using carboxylic acids as coupling partners in cross-coupling reactions.

Organosulfur Chemistry: Expanding the Frontiers of SO2

Utilization in Catalytic Synthetic Transformations

Sulfonyl-containing compounds, represent an important class of substances that have found widespread application in many areas varying from materials science and agrochemical development, to medicinal chemistry and organic chemistry where they function as important building blocks or as highly specialized reagents for synthetic applications.

The most prevalent compounds that contain the SO2-motif are sulfones, sulfonamides, sultams, sulfonic acids, sulfonates, sultones and sulfonyl halides, among others. Sulfur dioxide (SO2) has been recognized as major environmental pollutant that has several adverse effects on the human health. Thus, our group focuses on the development of catalytic transformations of this environmental pollutant into value-added compounds.