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Functionalization of Carbon–Hydrogen Bonds Through Transition Metal Carbenoid Insertion

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C-H Activation

Part of the book series: Topics in Current Chemistry ((TOPCURRCHEM,volume 292))

Abstract

The functionalization of carbon–hydrogen bonds through transition metal carbenoid insertion is becoming a powerful method for the construction of new carbon–carbon bonds in organic synthesis. This chapter will highlight recent developments in this field, while placing it within its historical context. Intramolecular carbenoid C–H insertion will be covered first, focusing on formation of three- and six-membered rings, as well as the use of nontraditional substrates. Additionally, the most recent progress in asymmetric catalysis will be discussed. The bulk of the chapter will concentrate on intermolecular transformations, emphasizing both the effect of substrate structure and the influence of carbene substituent electronics on the regioselectivity of the reactions. Vinyldiazoacetates will be covered as a distinct class of carbenoid precursor, as they have been shown to initiate a variety of unique transformations, such as the combined C–H activation/Cope rearrangement. Finally, the synthetic utility of carbenoid C–H insertion reactions, both intra- and intermolecular, will be displayed through their use in the total syntheses of a number of natural products and pharmaceuticals.

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Abbreviations

2,2-DMB:

2,2-Dimethylbutane

ad:

Adamantyl

BOX:

Bis(oxazoline)

cy:

Cyclohexyl

de:

Diastereomeric excess

dr:

Diastereomeric ratio

EDA:

Ethyl diazoacetate

EDG:

Electron donating group

ee:

Enantiomeric excess

EWG:

Electron withdrawing group

hfacac:

Hexafluoroacetylacetonate

mes:

Mesityl (2,4,6-trimethylbenzene)

pABSA:

p-Acetamidobenzenesulfonyl azide

por*:

Chiral porphyrin ligand

TFT:

α,α,α-Trifluorotoluene

Tp:

Trispyrazolylborate

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Acknowledgments

We wish to acknowledge members of the Davies group for their careful proofreading of this chapter and their valuable suggestions. The Davies group conducted much of the work related to the donor/acceptor carbenoids and we greatly appreciate the outstanding contributions to this program of past and current group members. The National Science Foundation and the National Institutes of Health generously funded the research conducted in the Davies group.

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Authors and Affiliations

  1. Department of Chemistry, Emory University, 1515 Dickey Drive, Atlanta, GA, 30322, USA

    Huw M. L. Davies

  2. University at Buffalo, The State University of New York, Buffalo, NY, USA

    Allison R. Dick

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Correspondence to Huw M. L. Davies .

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Editors and Affiliations

  1. Scripps Research Institute, N.Torrey Pines Rd. 10550, La Jolla, 92037, USA

    Jin-Quan Yu

  2. College of Chemistry, Peking University, Chengfu Road 202, Beijing, 100871, China, People's Republic

    Zhangjie Shi

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Davies, H.M.L., Dick, A.R. (2009). Functionalization of Carbon–Hydrogen Bonds Through Transition Metal Carbenoid Insertion. In: Yu, JQ., Shi, Z. (eds) C-H Activation. Topics in Current Chemistry, vol 292. Springer, Berlin, Heidelberg. https://doi.org/10.1007/128_2009_11

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