Visible light mediated intermolecular [3 + 2] annulation of cyclopropylanilines with alkynes

• Theresa H. Nguyen,
• Soumitra Maity and
• Nan Zheng

Beilstein J. Org. Chem. 2014, 10, 975–980, doi:10.3762/bjoc.10.96

• -iodobenzene (19) and cycloproylamine, 2-bromo-N-cyclopropylaniline (20) was prepared in 75% yield via the Buchwald–Hartwig amination [39][40]. The [3 + 2] annulation of 2-bromo-N-cyclopropylaniline (20) and phenylacetylene (2) was performed using the optimized catalyst system to provide cyclic allylic amine

An overview of the synthetic routes to the best selling drugs containing 6-membered heterocycles

• Marcus Baumann and
• Ian R. Baxendale

Beilstein J. Org. Chem. 2013, 9, 2265–2319, doi:10.3762/bjoc.9.265

Synthesis of 5-oxyquinoline derivatives for reversal of multidrug resistance

• Torsten Dittrich,
• Nils Hanekop,
• Nacera Infed,
• Lutz Schmitt and
• Manfred Braun

Beilstein J. Org. Chem. 2012, 8, 1700–1704, doi:10.3762/bjoc.8.193

• precursor 2c was obtained by an N-arylation, as described in the literature.[21] A modified Buchwald–Hartwig amination reaction using tri-tert-butylphosphane as a ligand at palladium [22] was applied in order to couple 4-methylphenyl bromide and 4-fluorophenyl bromide with Boc-protected aminopiperidines 17

Extending the utility of [Pd(NHC)(cinnamyl)Cl] precatalysts: Direct arylation of heterocycles

• Anthony R. Martin,
• Anthony Chartoire,
• Alexandra M. Z. Slawin and
• Steven P. Nolan

Beilstein J. Org. Chem. 2012, 8, 1637–1643, doi:10.3762/bjoc.8.187

• ) (Figure 1). Complexes 1 and 2 are commercially available and have proven to be highly efficient in Suzuki–Miyaura coupling and Buchwald–Hartwig amination reactions [17][18][19][20]. We have also evaluated the recently reported [Pd(IPr*)(cin)Cl] (3), which has shown potency in Suzuki–Miyaura couplings [21

Double N-arylation reaction of polyhalogenated 4,4’-bipyridines. Expedious synthesis of functionalized 2,7-diazacarbazoles

• Mohamed Abboud,
• Emmanuel Aubert and
• Victor Mamane

Beilstein J. Org. Chem. 2012, 8, 253–258, doi:10.3762/bjoc.8.26

• -diazacarbazole by using a palladium-catalyzed double N-arylation of 4,4’-dichloro-3,3’-bipyridine, itself obtained after a long reaction sequence [25][26][27]. In another patent, an intramolecular Buchwald–Hartwig amination [28][29] was used to generate a 2,7-diazacarbazole derivative in low yield [30]. Recently

Amines as key building blocks in Pd-assisted multicomponent processes

• Didier Bouyssi,
• Nuno Monteiro and
• Geneviève Balme

Beilstein J. Org. Chem. 2011, 7, 1387–1406, doi:10.3762/bjoc.7.163

• preparation of various 2,3-disubstituted indole derivatives 62 (Scheme 27). Amines as coupling partners through Buchwald–Hartwig amination Other strategies used for the palladium-mediated three-component preparation of substituted indole derivatives involve an efficient Buchwald–Hartwig amination as the key

• coupling leading to a mono-alkynylated product, followed by an intermolecular Buchwald–Hartwig amination and a subsequent intramolecular amination. This Pd-catalyzed tandem coupling reaction allows the preparation of a variety of 2-alkynylindoles 64 (Scheme 28). An elegant three-component process based on

Palladium- and copper-mediated N-aryl bond formation reactions for the synthesis of biological active compounds

• Carolin Fischer and
• Burkhard Koenig

Beilstein J. Org. Chem. 2011, 7, 59–74, doi:10.3762/bjoc.7.10

• -aryl bond formation, and many examples illustrate their wide application in organic synthesis. The chelating phosphines BINAP, DPPF [17] and DtBPF [18], commonly used for the Buchwald–Hartwig amination, were recently displaced by the biaryl-(dialkyl)phosphine or arylphosphinepyrrole ligands [18][19][20

• ]. Industrial scale-up of these methods has already been applied on the 100 kg scale for arylpiperazines and different diarylamines [21]. In addition, Nolan et al. and Organ et al. have reported Pd-N-heterocyclic carbene (NHC)-catalysed Buchwald–Hartwig amination protocols that provide access to a range of