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Scheuermann, J.  et al.: 2024 Science of Synthesis, 2023/5: DNA-Encoded Libraries DOI: 10.1055/sos-SD-241-00025
DNA-Encoded Libraries

2.2 Metal-Promoted DEL-Compatible C—C Bond Forming Reactions

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Book

Editors: Scheuermann, J. ; Li, Y. 

Authors: Barluenga, S. ; Bassi, G. ; Brunschweiger, A. ; Cai, B. ; Cazzamalli, S. ; Chheda, P. ; Cui, M. ; Cui, W. ; Fang, X. ; Farrera-Soler, L. ; Favalli, N. ; Feng, J.; Foley, T. L. ; Franzini, R. M. ; Georgiev, T. ; Gillingham, D. ; Gloger, A. ; Graham, J. D. ; Granados, A. ; Heiden, S.; Hou, W. ; Huang, Y. ; Keefe, A. D. ; Krusemark, C. J. ; Li, X. ; Li, Y. ; Lin, W. ; Litovchick, A.; Liu, G. ; Lu, X. ; Lucaroni, L. ; Ma, P. ; Migliorini, F. ; Molander, G. A. ; Neri, D. ; Nie, Q. ; Oehler, S. ; Prati, L. ; Puglioli, S. ; Reddavide, F. V. ; Satz, A. L. ; Sauter, B. ; Scheuermann, J. ; Schuman, D.; Simmons, N. ; Stanway-Gordon, H. A. ; Su, W. ; Sun, J. ; Thompson, M.; Vummidi, B. R.; Wang, X. ; Wang, Y. ; Wang, Z. ; Waring, M. J. ; Willems, S.; Winssinger, N. ; Xia, B. ; Xiong, F. ; Xu, H. ; Xu, L. ; Yang, G. ; Zhang, G. ; Zhang, Y. ; Zhou, Y. 

Title: DNA-Encoded Libraries

Print ISBN: 9783132455221; Online ISBN: 9783132437357; Book DOI: 10.1055/b000000342

1st edition © 2024. Thieme. All rights reserved.
Georg Thieme Verlag KG, Stuttgart

Subjects: Organic Chemistry

Science of Synthesis Reference Libraries



Parent publication

Title: Science of Synthesis

DOI: 10.1055/b-00000101

Series Editors: Fürstner, A. (Editor-in-Chief); Carreira, E. M.; Faul, M.; Kobayashi, S.; Koch, G.; Molander, G. A.; Nevado, C.; Trost, B. M.; You, S.-L.

Type: Multivolume Edition

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Abstract

DNA-encoded library (DEL) technology relies on the availability of robust and DNA-compatible chemical transformations. Metal-promoted C—C bond forming reactions are widely applied for the synthesis of fine chemicals such as pharmaceuticals. However, their application in DEL technology represents a challenge due to the use of metal catalysts, high temperatures, and organic solvents. In this chapter, we report tailored conditions for the on-DNA application of the Suzuki, Sonogashira, Heck, and Giese reactions. The conditions presented in this chapter have been systematically explored across different DEL designs and structurally-diverse building blocks. By providing a comprehensive insight into the practical implementation of these metal-promoted C—C bond cross-coupling reactions, this review aims at expanding and promoting the application of these transformations in DEL construction.

Key words

DNA-encoded libraries - C—C bond formation - cross-coupling reactions - DEL synthesis - DNA-compatible reactions - Giese reaction - Heck reaction - Sonogashira coupling - Suzuki coupling - metal-catalyzed reactions
 
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