Fürstner / Schaumann Science of Synthesis Knowledge Updates: 2015/2

1. Auflage 2015
ISBN: 978-3-13-198481-4
Verlag: Thieme
Format: PDF
Kopierschutz: Adobe DRM (»Systemvoraussetzungen)

E-Book, Englisch, 536 Seiten, PDF

Reihe: Science of Synthesis

The Science of Synthesis Editorial Board, together with the volume editors and authors, is constantly reviewing the whole field of synthetic organic chemistry as presented in and evaluating significant developments in synthetic methodology. Highlights of this volume of Knowledge Updates include chapters on the chemistry of platinum and iridium complexes, as well as the synthesis of triazoles, phthalazines, and quinazolines, heterosubstituted alkynes, nitrosoalkenes, and various haloalkane compounds.

Zielgruppe

Wissenschaftler

Autoren/Hrsg.

Fürstner, Alois

Schaumann, Ernst

Weitere Mitwirkende

Carreira, Erick M.

Decicco, Carl P.

Fürstner, Alois

Molander, Gary A.

Schaumann, Ernst

Fachgebiete

• Naturwissenschaften Chemie Organische Chemie

Leseproben

Abstracts

1.3.6 Organometallic Complexes of Platinum

This chapter is an update to the earlier contribution (Section 1.3) describing methods for the synthesis of organometallic complexes of platinum and related applications in catalytic reactions using organoplatinum complexes. Recently, organometallic complexes of platinum have been used in many areas, including as medical or luminescent materials.

Keywords: Diels–Alder cycloaddition · allene complexes · dinuclear complexes · anticancer agents · allyl complexes · metallacycles · alkyne complexes · catalytic reactions · selenaplatinacycles · dicationic complexes

1.6.9 Organometallic Complexes of Iridium

This chapter is an update to the earlier contribution (Section 1.6) that covers literature from 1999 to the first half of 2013. While Section 1.6 provided a fantastic overview of the different types of organometallic complexes of iridium and their preparation, this contribution aims at focusing more on their applications in homogeneous catalysis.

Keywords: iridium complexes · catalysis · borylation · oxidation · hydroamination · dehydrogenative coupling · hydrogenation · transfer hydrogenative coupling · transfer hydrogenation · allylic substitution · isomerization · oligomerization

13.13.6 1,2,3-Triazoles

This chapter is an update to the earlier contribution (Section 13.13) describing methods for the synthesis of 1,2,3-triazoles. Recent interest in this area has mainly been generated by the discovery that copper(I)-catalyzed azide–alkyne cycloaddition (CuAAC) and ruthenium (II)-catalyzed azide–alkyne cycloaddition (RuAAC) regioselectively afford 1,4- or 1,5-disubstituted 1,2,3-triazoles in high yields under mild conditions. This review focuses on the contributions published between 2002 and 2013.

Keywords: 1,2,3-triazoles · azides · alkynes · click chemistry · Huisgen reaction · 1,3-dipolar cycloadditions · copper catalysts · ruthenium catalysts

16.10.5 Phthalazines

This chapter is an update to the earlier contribution (Section 16.10) concerning the synthesis and reactions of phthalazines. Literature from 2004 to early 2014 has been considered. The major focus since the initial publication involves phthalazine substituent modification rather than the synthesis of phthalazine rings.

Keywords: phthalazines · 2,3-dihydrophthalazine-1,4-diones · multicomponent reactions · cyclization · heteroarylation · cross coupling · hypervalent iodine

16.13.5 Quinazolines

This chapter is an update to the earlier contribution (Section 16.13) describing methods for the synthesis of quinazolines. It summarizes new technologies and surveys the literature published in the period 2002–2012.

Keywords: quinazolines · quinazolinones · quinazolinediones · nitriles · isocyanides · annulation · rearrangement · multicomponent condensation · cyclization · ionic liquids · copper(I) iodide · solid-phase synthesis · C—H insertion · carbon dioxide fixation · solvent free

24.4.2.3 1-(Organooxy) alk-1-ynes and 1-(Heterooxy) alk-1-ynes

This manuscript is an update to the earlier contribution (Section 24.4.2) describing methods for the synthesis of 1-(organooxy) alk-1-ynes and 1-(heterooxy) alk-1-ynes. The original contribution describes the synthesis of six subgroups: alk-1-ynyl , -dialkylcarbamates, carboxylates, ethers, sulfonates, and dialkyl phosphonates as well as 1-siloxyalk-1-ynes. However, during the period covered in this update (2005–2014), new contributions have only been made in the field of alk-1-ynyl ethers and 1-siloxyalk-1-ynes. These methodologies, primarily methods centering on elimination reactions, are covered in this chapter, along with a short description of the applications of these two types of compound.

Keywords: alkynyl ethers · siloxyalkynes · elimination · Meyer–Schuster rearrangement · metal catalysis

24.4.4.4 1-Nitrogen-Functionalized Alk-1-ynes

This chapter is an update of the earlier contributions (Sections 24.4.4.1–24.4.4.3) describing methods for the synthesis of ynamines, and especially those alk-1-yn-1-amines that bear electron-withdrawing units such as -acyl and -sulfonyl groups. Compounds with C?C bonds directly connected to azido or nitro functionalities are likewise updated, whereas the chemistry of -alk-1-ynyl-substituted sulfoximines and isocyanates is described for the first time. The update focuses on new developments published in the period 2004–2014.

Keywords: alkynes · alkynylation · amines · azides · carboxamides · copper catalysis · dehydrohalogenation · isocyanates · nitro compounds · oxazolidinones · sulfonamides · sulfoximines

24.4.5.3 1-Phosphorus-Functionalized Alk-1-ynes

This chapter is an update to the earlier contribution (Section 24.4.5) describing methods for the synthesis of 1-phosphorus-functionalized alk-1-ynes. The focus is on the literature published in the period 2006–2014.

Keywords: alkynylation · oxidative coupling · metal catalysis · (alk-1-ynyl) benziodoxolone reagents · alkynyl protecting groups

33.4.2.3 1-Nitrosoalkenes

This chapter deals with the generation of nitrosoalkenes from suitable precursors and their application as synthetically useful key intermediates in organic synthesis, including the synthesis of natural products and biologically active compounds. This is an update to Section 33.4.2, covering selected relevant literature that has been reported since 2007.

Keywords: nitrosoalkenes · dehydrohalogenation · halooximes · nitroalkene reduction · [4 + 2] cycloaddition · [3 + 2] cycloaddition · hetero-Diels–Alder · -hydroxypyrroles · natural products

33.5.7.2 1,2-Dihydrophosphetes and Derivatives

This chapter is an update to the earlier contribution (Section 33.5.7) describing methods for the synthesis of 1,2-dihydrophosphetes. It focuses on the literature published in the period 2004–2015.

Keywords: vinyl compounds · titanium complexes · phosphorus heterocycles · phosphine oxides · metallacycles

33.5.8.2 2,3-Dihydro-1-phospholes and Derivatives

This chapter is an update to the earlier contribution (Section 33.5.8) describing methods for the synthesis of 2,3-dihydro-1-phospholes. It focuses on the literature published in the period 2004–2015.

Keywords: zirconium complexes · phosphorus heterocycles · phosphines · metallacycles · metathesis

33.5.9.2 1,2,3,4-Tetrahydrophosphinines and Derivatives

This chapter is an update to the earlier contribution (Section 33.5.9) describing methods for the synthesis of 1,2,3,4-tetrahydrophosphinines. It focuses on the literature published in the period 2004–2015.

Keywords: enamines · bromine compounds · phosphorus heterocycles · phosphonium salts · cyclization

33.5.10.2 1,4-Dihydrophosphinines and Derivatives

This chapter is an update to the earlier contribution (Section 33.5.10) describing methods for the synthesis of 1,4-dihydrophosphinines. It focuses on the literature published in the period 2004–2015.

Keywords: phosphorus heterocycles · phosphinic acids · unsaturated compounds · ring expansion · carbenes

35.1.1.1.9 Synthesis by Substitution of Hydrogen