A recent overview on the synthesis of 1,4,5-trisubstituted 1,2,3-triazoles

• Pezhman Shiri,
• Ali Mohammad Amani and
• Thomas Mayer-Gall

Beilstein J. Org. Chem. 2021, 17, 1600–1628, doi:10.3762/bjoc.17.114

• found to be efficient for a practical pathway to 5‐alkynyl-1,2,3-triazoles 69 from organic azides 67, alkynes 66, and 1-bromoalkynes 68. To test the scope of this reaction, a number of alkyl- and (hetero)aryl-substituted alkynes as well as (alkyl)aryl azides have been used in this reaction, affording 5

• -alkynyl-1,2,3-triazoles 69 in good to high yield. Moreover, heteroaryl-substituted 1-bromoalkyne, iPr3Si-substituted 1-bromoalkyne, and a number of alkyl-substituted 1-bromoalkynes were treated in this process to provide the corresponding products with good to high yield (Scheme 21) [51]. It is noteworthy

Coupling of α,α-difluoro-substituted organozinc reagents with 1-bromoalkynes

• Artem A. Zemtsov,
• Alexander D. Volodin,
• Vitalij V. Levin,
• Marina I. Struchkova and
• Alexander D. Dilman

Beilstein J. Org. Chem. 2015, 11, 2145–2149, doi:10.3762/bjoc.11.231

• Federation 10.3762/bjoc.11.231 Abstract α,α-Difluoro-substituted organozinc reagents generated from conventional organozinc compounds and difluorocarbene couple with 1-bromoalkynes affording gem-difluorinated alkynes. The cross-coupling proceeds in the presence of catalytic amounts of copper iodide in

• dimethylformamide under ligand-free conditions. Keywords: 1-bromoalkynes; cross-coupling; organofluorine compounds; organozinc reagents; Introduction gem-Difluorinated organic compounds have attracted increasing attention nowadays due to their applicability in medicinal chemistry [1][2] and other fields. Indeed

• nitrostryrenes (with the NO2 serving as a leaving group) [20], were employed. Herein, we report that 1-bromoalkynes, which are known to be involved in reactions with various organometallic compounds [22][23][24][25][26][27], can be used as suitable coupling partners for difluorinated organozinc compounds 2. This

Preparation of phosphines through C–P bond formation

• Iris Wauters,
• Wouter Debrouwer and
• Christian V. Stevens

Beilstein J. Org. Chem. 2014, 10, 1064–1096, doi:10.3762/bjoc.10.106

Advancements in the mechanistic understanding of the copper-catalyzed azide–alkyne cycloaddition

• Regina Berg and
• Bernd F. Straub

Beilstein J. Org. Chem. 2013, 9, 2715–2750, doi:10.3762/bjoc.9.308

• 1,2,3-triazoles. In 2005, the group of Rutjes reported the synthesis of 5-bromo-1,4-disubstituted-1,2,3-triazoles starting from 1-bromoalkynes [155]. In their optimized procedure, the bromoalkyne reacts with an azide in the presence of 5 mol % copper(I) iodide and 5 mol % copper(II) acetate in THF at 50

• , exchange of the halide group when 1-bromoalkynes are reacted with azides in the presence of copper(I) iodide [155] as observed by Rutjes et al. cannot be explained by this pathway. In 2006, the group of Nolan presented the synthesis of 1,4,5-trisubstituted-1,2,3-triazoles by cycloaddition reactions between