Reactions of metallocarbenes derived from N-sulfonyl-1,2,3-triazoles

Metal-stabilized carbenes derived from diazo compounds have become broadly useful reactive intermediates for organic synthesis. This tutorial review will describe the recent advances in using N -sulfonyl-1,2,3-triazoles as precursors for the formation of metal-bound imino carbene intermediates. Thes...

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Published inChemical Society reviews Vol. 43; no. 15; pp. 5151 - 5162
Main Authors Davies, Huw M. L, Alford, Joshua S
Format Journal Article
LanguageEnglish
Published England 07.08.2014
Subjects
Carbenes
Catalysis
Catalysts
Formations
Level (quantity)
Precursors
Synthesis
Transformations
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Summary:Metal-stabilized carbenes derived from diazo compounds have become broadly useful reactive intermediates for organic synthesis. This tutorial review will describe the recent advances in using N -sulfonyl-1,2,3-triazoles as precursors for the formation of metal-bound imino carbene intermediates. These intermediates undergo a variety of synthetically useful transformations, which include transannulation reactions to generate new heterocycles, cyclopropanation and subsequent ring expansions, ylide formation with subsequent rearrangements, and C-H functionalization. Furthermore, many of these transformations can be conducted with high levels of enantioselectivity by use of chiral rhodium( ii ) catalysts. Metal-stabilized carbenes derived from N -sulfonyl triazoles have become broadly useful reactive intermediates for organic synthesis.
Bibliography:Huw M. L. Davies was born in Aberystwyth, Wales, UK. He began his independent academic career at Wake Forest University. In 1995 he moved to the University at Buffalo, the State University of New York, where he held the positions of UB Distinguished Professor and Larkin Professor of Organic Chemistry. In 2008, he joined the faculty at Emory University as the Asa Griggs Candler Professor of Chemistry. His research program covers design of chiral catalysts, development of new synthetic methodology, total synthesis of biologically active natural products, and development of chiral therapeutic agents. A major current research theme in his group is catalytic asymmetric C-H functionalization. He is the Director of the National Science Foundation Center on Selective C-H Functionalization.
Joshua S. Alford graduated with a MS degree from Missouri State University in 2008, under the mentorship of Dr Chad Stearman. He started his PhD studies in 2009 under the supervision of Prof. Huw M. L. Davies at Emory University. His research interests include the use of N-sulfonyl triazoles for heterocycle synthesis, expanding the scope of donor/acceptor metallocarbenes, and the synthesis of novel therapeutic agents for drug abuse.
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ISSN:0306-0012
1460-4744
DOI:10.1039/c4cs00072b