Grignard reagents undergo conjugate addition to thiochromones catalyzed by copper salts to afford 2-substituted-thiochroman-4-ones, both 2-alkylthiochroman-4-ones and thioflavanones (2-arylthiochroman-4-ones), in good yields with trimethylsilyl chloride (TMSCl) as an additive. The best yields of 1,4-adducts can be attained with CuCN∙2LiCl as the copper source. Excellent yields of 2-alkyl-substituted thiochroman-4-ones and thioflavanones (2-aryl substituted) are attained with a broad range of Grignard reagents. This approach works well with both alkyl and aromatic Grignard reagents, thus providing a unified synthetic approach to privileged 2-substituted thiochroman-4-ones and a potential valuable precursor for further synthetic applications towards many pharmaceutically active molecules. The use of commercially available and/or readily prepared Grignard reagents will expedite the synthesis of a large library of both 2-alkyl substituted thiochroman-4-ones and thioflavanones for additional synthetic applications.

Undergraduate research is well recognized as an effective high-impact educational practice associated with student success in higher education. Actively engaging students in research experiences is considered as one of the several high-impact practices by many agencies including the American Chemical Society. Developing and maintaining an active undergraduate research program benefits both the faculty and students especially those from under-represented minority groups (URM). The infusion of research experiences into undergraduate curriculum enables students from all backgrounds to develop independent critical thinking skills, written and oral communications skills that are very important for successful careers in “STEM” area. Several strategies and activities such as a Peer Mentoring Program (PMP), funded research activities, the infusion of research into organic chemistry labs, undergraduate professional development, research group meetings, presentations at regional/national conferences, and publishing as co-authors on peer-review papers are vital in creating a welcoming research group that promotes the diversity, equity, and inclusion in organic chemistry education. The experiences working on funded research projects, presenting their research data at conferences and publishing papers as co-authors will greatly increase the under-represented minority (URM) students’ chance in landing a job or getting admitted into graduate/professional programs in STEM area.