N-aryl heterocycles via coupling reactions with arylboronic acids

Mederski, Werner W. K. R.; Lefort, Marina; Germann, Martina; Kux, Dieter

doi:10.1016/s0040-4020(99)00752-8

Cited by 109 publications

(52 citation statements)

References 17 publications

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“…[37] Notably, in this transformation it was possible to selectively form the N-aryl product 69 with none of the corresponding Oarylated product being observed. Under different conditions (KOtBu, DMF), a mixture of N-/O-arylated products (2:1) was observed.…”

Section: Applications: Medicinal Chemistry and Solid-phasementioning

confidence: 99%

Modern Synthetic Methods for Copper‐Mediated C(aryl)O, C(aryl)N, and C(aryl)S Bond Formation

Ley,

Thomas

2003

Angew Chem Int Ed

2,518

816

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The copper-mediated C(aryl)[bond]N, C(aryl)[bond]O, and C(aryl)[bond]S bond formation is an important transformation and has been developed to include a wide range of substrates. This Review highlights the recent developments in the copper-mediated (both stoichiometric and catalytic) reactions of aryl boronic acids, aryl halides, iodonium salts, siloxanes, stannanes, plumbanes, bismuthates, and trifluoroborate salts as aryl donors. In particular, the recent introduction of boronic acids as reaction partners in both O- and N-arylation has been a significant discovery and will occupy centre-stage in this review. Clear improvements can be obtained by the correct choice of copper source, base, ligands, and other additives. Mechanistic investigations should provide insight into the catalytically active species, which would aid in the development of milder, more-efficient methods.

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Section: Applications: Medicinal Chemistry and Solid-phasementioning

confidence: 99%

Modern Synthetic Methods for Copper‐Mediated C(aryl)O, C(aryl)N, and C(aryl)S Bond Formation

Ley,

Thomas

2003

Angew Chem Int Ed

2,518

816

View full text Add to dashboard Cite

show abstract

“…One post-cleavage methylation has also been reported (Scheme 17). 16 On the other hand, palladium 33,34 or copper-catalysed 35 Narylations reported in solution have not been reported on solid phase so far. Maybe, in the future, these reactions will be adapted to solid-phase chemistry and also alkylations or acylations with groups that have a directing effect toward C-2 lithiation.…”

Section: Modification Of Indoles By Substitution At Nitrogenmentioning

confidence: 99%