Palladium-Catalyzed Nonclassical Dicarbofunctionalization of Skipped Dienes
Open Access
Author:
Chesley, Lucas
Graduate Program:
Chemistry (MS)
Degree:
Master of Science
Document Type:
Master Thesis
Date of Defense:
June 16, 2021
Committee Members:
Philip Bevilacqua, Program Head/Chair Ramesh Giri, Thesis Advisor/Co-Advisor Eric Nacsa, Committee Member Elizabeth A Elacqua, Committee Member Emily E Weinert, Committee Member
1,3-Disubstituted cyclohexanes are a set of architectures that have been gaining popularity in natural products and bioactive compounds. While 1,2-difunctionalization of alkenes has been extensively studied, the access of functionalization at nonclassical sites remains an emerging area of significance. This work describes a palladium-catalyzed vinylarylation of 1,4-cyclohexadiene at the nonclassical 1,3-positions from readily available starting materials using arylboronic acids and alkenyl triflates. Previously, β-H elimination has been a challenging step that has been avoided in classical alkene dicarbofunctionalization. However, here we seek to continue our work of utilizing β-H elimination in a positive manner to allow for the access of nonclassical C(sp3) sites for dicarbofunctionalization. This nonclassical functionalization can help open up new ways to view alkenes as an access group for functionalizing molecules in ways that would have otherwise required significant synthetic steps.
