Palladium- and nickel-catalyzed cascade enantioselective ring-opening/coupling reactions of cyclobutanones

The chemistry of small ring compounds is an intriguing subject in organic chemistry. As the smallest stable cyclic aliphatic ketones, cyclobutanones have garnered tremendous attention owing to their intrinsic high reactivity such as transition-metal catalyzed C-C bond cleavage. In this context, tran...

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Published inChemical communications (Cambridge, England) Vol. 59; no. 23; pp. 3373 - 3382
Main Authors Cao, Jian, Xu, Li-Wen
Format Journal Article
LanguageEnglish
Published England Royal Society of Chemistry 16.03.2023
Subjects
Cascade chemical reactions
Chemical reactions
Coupling (molecular)
Covalent bonds
Cyclic compounds
Cycloaddition
Ductile-brittle transition
Enantiomers
Ketones
Natural products
Nickel
Organic chemistry
Palladium
Ring opening
Transition metals
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Summary:The chemistry of small ring compounds is an intriguing subject in organic chemistry. As the smallest stable cyclic aliphatic ketones, cyclobutanones have garnered tremendous attention owing to their intrinsic high reactivity such as transition-metal catalyzed C-C bond cleavage. In this context, transition-metal catalyzed formal cycloaddition of cyclobutanones via a "cut and sew" strategy has gained marvelous advances. In contrast, an alternative reaction paradigm, i.e. , transition-metal catalyzed ring-opening reactions of cyclobutanones, is still underdeveloped. This feature article aims to summarize our efforts in developing enantioselective palladium-catalyzed ring-opening/coupling reactions and recently emerging nickel-catalyzed ring-opening/reductive coupling reactions of cyclobutanones with a tethered aryl halide. The possible mechanisms are briefly showcased and the advantages and limitations of each strategy as well as their synthetic applications in the synthesis of natural products or bioactive compounds are presented. This article summarizes recent efforts in developing enantioselective palladium- and nickel-catalyzed ring-opening/coupling reactions of cyclobutanones with a tethered aryl halide.
Bibliography:Jian Cao was born in 1983 in Karamay City, China. He obtained his B.S. degree in 2005 and PhD in 2010 from Zhejiang University. Then he began his academic career at Hangzhou Normal University. He was a visiting scholar at the Ecole Polytechnique Fede rale de Lausanne (EPFL). He is currently an associate professor at Hangzhou Normal University. His research focuses on organosilicon chemistry and asymmetric catalysis.
Li-Wen Xu was born in Anhui and obtained his PhD in 2004 from the Lanzhou Institute of Chemical Physics in the Chinese Academy of Sciences. He was an associate research professor at the State Key Laboratory for Oxo Synthesis and Selective Oxidation (OSSO) from 2004 to 2006. He was a postdoctoral fellow at the CNRS in France (2005-2006), the National University of Singapore (2007-2008), and the University of Tokyo (2008-2009) and was appointed as a full professor at Hangzhou Normal University in 2009. He is currently the Dean of the Graduate School of Hangzhou Normal University. His research interests include asymmetric catalysis and organosilicon chemistry.
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ISSN:1359-7345
1364-548X
1364-548X
DOI:10.1039/d3cc00205e