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Christmann, M. et al.: 2020 Science of Synthesis: Knowledge Updates 2020/2 DOI: 10.1055/sos-SD-110-01749
Knowledge Updates 2020/2

10.4 Product Class 4: Benzo[b]thiophenes

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Editors: Christmann, M.; Huang, Z.; Joule, J. A.; Li, C.-J.; Li, J.; Marschner, C.; Petersson, E. J.; Reißig, H.-U.; Schaumann, E.; Terent'ev, A. 

Authors: Ambhaikar, N.; Campagne, J.-M.; Celik, I.; Dembitsky, V.; Graham, M.; Holzschneider, K.; Jaschinski, M.; Kipke, W.; Kirsch, S.; Kunz, K.; Leclerc, E.; Li, G.; Li, Z.; Makow, J.; Müller, T.; Ochoa, C. I.; Ramirez y Medina, I.-M. .; Rayner, C. M.; Staubitz, A.; Sun, X.-L.; Szostak, M.; Tambar, U. K.; Tian, T.; Tong, M.; Wang, X.-Y.; Yaremenko, I.; Yoshikai, N.

Title: Knowledge Updates 2020/2

Print ISBN: 9783132435612; Online ISBN: 9783132435636; Book DOI: 10.1055/b000000103

1st edition © 2020 Thieme. All rights reserved.
Georg Thieme Verlag KG, Stuttgart

Subjects: Organic Chemistry;Chemical Reactions, Catalysis;Organometallic Chemistry;Laboratory Techniques, Stoichiometry

Science of Synthesis Knowledge Updates



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.; Nevado, C.; Trost, B. M.; You, S.

Type: Multivolume Edition

Also available at
 

Abstract

This chapter is a revision of the earlier Science of Synthesis Section 10.4. It describes methods for the synthesis of benzo[b]thiophenes and related compounds by ring closure or by modification of existing substituent(s) on the benzo[b]thiophene skeleton. Ring-closure methods typically involve the formation of the five-membered ring starting from benzene derivatives bearing substituents such as halogen, alkenyl, alkynyl, or sulfanyl groups at appropriate positions. Ring closure to form the benzene ring can also be achieved using suitably substituted thiophene derivatives. In particular, a number of new methods involving metal-catalyzed C-C and C–S bond formation that have been developed since the previous review are included. Recent years have also witnessed substantial progress in the methods available to directly introduce new substituents to the 2- and 3-positions of benzo[b]thiophenes through metal-catalyzed C-H bond functionalization, and these are included in this chapter.

Key words

benzo compounds - benzo[b]thiophenes - thiophenes - sulfides - alkenes - alkynes - halo compounds - carbonyl compounds - palladium catalysis - copper catalysis - organolithium compounds - cyclization - ring closure - annulation - cross-coupling reactions - C-H activation reactions
 
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