Congested C(sp3)-Rich Architectures Enabled by Iron-catalyzed Conjunctive Alkylation
M. J. Koh, X. Zhang and P. L. Holland describe the synthesis of congested C(sp3)-rich architectures using Fe catalysis.
Transition metal-catalyzed cross-coupling has become a staple synthetic method for forming carbon–carbon bonds in the pharmaceutical industry. However, advancements in this field are largely focused on reactions involving sp2 carbons. Comparatively, sp3-hybridized substrates are less reactive due to their resistance to oxidative addition during cross-coupling. Due to the prevalence of densely functionalized sp3 environments in biologically active natural products, methods for assembling congested cores are urgently needed, particularly those that construct multiple sp3–sp3 (alkyl–alkyl) bonds. Professor Ming Joo Koh from the National University of Singapore stated that “a catalytic process that assembles multiple alkyl–alkyl bonds to afford densely substituted entities would empower users to access medicinally valuable but synthetically elusive C(sp3)-rich building blocks with sterically crowded stereocenters.”
Recently, the groups of Professor Koh, Dr. Xinglong Zhang [Institute of High Performance Computing, Agency for Science, Technology and Research (A∗STAR), Singapore] and Professor Patrick Holland (Yale University, USA) described an earth-abundant (terpyridine)iron-catalyzed strategy for the dialkylation of olefins using C(sp3)–Zn nucleophiles and sp3-hybridized electrophiles.
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