Science of Synthesis Knowledge Updates 2018

In 2018, thirty updated, revised and new contributions have been published as part of the Science of Synthesis Knowledge Updates. Highlights include: 

  • A major update on organobismuth compounds (A. Gagnon, E. Benoit, and A. Le Roch), covering both advances in their synthesis and their increasingly important applications in synthetic chemistry, for example in cross-coupling reactions.
  • Updates on the synthesis and applications of carbamic acids and esters and their heteroatom analogues (J. Podlech) and on tetraheterosubstituted methanes bearing a carbon—halogen bond (M. Kleoff, K. Omoregbee, and R. Zimmer).
  • Updates on alkenylsulfonic acids, alkenyl sulfones, alkenylsulfoximides, alkenylsulfinic acids, and alkenyl sulfoxides and sulfimides (R. Kawęcki).
  • A totally revised chapter on the synthesis of oxetanes and oxtan-3-ones (R. A. Croft and J. A. Bull).
  • A major revision of the chapter on benzo[c]furans or isobenzofurans (H Kwiecień), including 1,3-dihydrobenzo[c]furan-1(3H)-ones [also called 1,3-dihydroisobenzofuran-1(3H)-ones or phthalides]. While most benzo[c]furans are very reactive and can normally only be isolated after trapping (for example by Diels–Alder reaction with dienophiles), 1,3-diarylbenzo[c]furans are much more stable.
  • Updates on the synthesis of isoquinolinones (V. A. Glushkov and Yu. V. Shklyaev), thiocarbonic acids and derivatives (R. A. Aitken), S,N-acetals, and N,N-acetals (Y. Saikawa and M. Nakata), as well as the cyclic S,S-acetals 1,3-dithianes and 1,3-dithiepanes (Y. Mutoh) and the synthesis of phenols from nonaromatic precursors (C. González-Bello).
  • A major new chapter on carbolines or pyrido[X,Y-b]indoles (J. A. Joule), covering the synthesis of all four regioisomeric heterocyclic systems, which are found in both natural products and pharmaceuticals.
  • An introductory chapter on S,S-acetals (T.-Y. Luh and M.-k. Leung), describing their use as protecting groups for carbonyl compounds and as alternative functional groups for further transformations.
  • Chapters on the synthesis of 1,3-dithietanes and 1,3-dithiolanes (T.-Y. Luh, M.-k. Leung, and C.-M. Chou), the latter of which are particularly important as masked carbonyl compounds.
  • A new chapter on silver-promoted coupling reactions (J.-M. Weibel, A. Blanc, and P. Pale).
  • An update on 1-(organochalcogeno)alkynes (A. Ulfkjær and M. Pittelkow) covering sulfur-, selenium-, and tellurium-substituted alkynes, covering both the synthesis and applications of these molecules, which are of importance as building blocks and intermediates in organic synthesis.
  • Updates on the synthesis of phenols by substitution, elimination, rearrangement reactions, and on the modification of phenols (C. González-Bello). Phenols occur widely in natural and synthetic compounds and this chapter reviews new and improved approaches to this key functionality. An update on arylphosphinic acids and derivatives (D. Virieux, T. Ayad, J.-L. Pirat, and J.-N. Volle) covering progress made over the last decade in the synthesis of this important class of organophosphorus compound.
  • An update on the synthesis of heteroatom-substituted allenes (A. S. K. Hashmi) covering the synthesis of both the allene functionality and the installation of heteroatoms onto a pre-existing allene.
  • A new chapter on immobilized biocatalysts and their application in flow chemistry (M. Bajić, P. Žnidaršič-Plazl, M. Kingston, and V. Hessel). Both biocatalysis and flow chemistry have attracted intense interest recently and their combination allows the practitioner to achieve the exquiste selectivity associated with biocatalysts while taking advantage of the ease of separation and practical advantages offered by the use of a heterogeneous catalyst in a flow reactor.

A complete overview of all updated content published in 2018 is given in the tables of contents and abstracts.

Table of Contents:




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