Functionalization of heterocyclic compounds using polyfunctional magnesium and zinc reagents

• Paul Knochel,
• Matthias A. Schade,
• Sebastian Bernhardt,
• Georg Manolikakes,
• Albrecht Metzger,
• Fabian M. Piller,
• Christoph J. Rohbogner and
• Marc Mosrin

Beilstein J. Org. Chem. 2011, 7, 1261–1277, doi:10.3762/bjoc.7.147

• the most important procedures for the preparation of functionalized organzinc and organomagnesium reagents. In addition, new methods for the preparation of polyfunctional aryl- and heteroaryl zinc- and magnesium compounds, as well as new Pd-catalyzed cross-coupling reactions, are reported herein

• . Experimental details are given for the most important reactions in the Supporting Information File 1 of this article. Keywords: cross-coupling; heterocycles; insertion; metalation; organomagnesium; organozinc; Introduction The functionalization of heterocyclic scaffolds is an important task in current

• organomagnesium reagents in this short review. Although, these reagents were introduced to synthetic organic chemistry at the turn of the 20th century, they are now more than ever essential organometallic intermediates. The progress in the 5 last years in our laboratories shows that much is still unknown in this

Homocoupling of aryl halides in flow: Space integration of lithiation and FeCl₃ promoted homocoupling

• Aiichiro Nagaki,
• Yuki Uesugi,
• Yutaka Tomida and
• Jun-ichi Yoshida

Beilstein J. Org. Chem. 2011, 7, 1064–1069, doi:10.3762/bjoc.7.122

• transmetalation of the aryl group from lithium to iron followed by reductive elimination of the homo-coupling product seems to be plausible, while a similar mechanism is proposed for homo-coupling of organomagnesium compounds with FeCl3 [19][20]. The regiospecificity of the coupling is consistent with this

A practical route to tertiary diarylmethylamides or -carbamates from imines, organozinc reagents and acyl chlorides or chloroformates

• Erwan Le Gall,
• Antoine Pignon and
• Thierry Martens

Beilstein J. Org. Chem. 2011, 7, 997–1002, doi:10.3762/bjoc.7.112

• inter- or intramolecularly [8][9][10][11][12][13][14][15][16]. However, an increased range of aromatic moieties can be introduced through the use of organometallic compounds. The most commonly employed reagents are organoindium [17][18], organolithium [19][20], organomagnesium [21][22], organotin [23

Recent advances in carbocupration of α-heterosubstituted alkynes

• Ahmad Basheer and
• Ilan Marek

Beilstein J. Org. Chem. 2010, 6, No. 77, doi:10.3762/bjoc.6.77

• undergoes a subsequent thermal [3,3]-sigmatropic rearrangement to give the corresponding nitrile 27. The presence of the organomagnesium group on 26 is essential for the rearrangement to proceed in good yield (Scheme 12). The silylcupration of N-1-alkynylsulfonylamides 28 led to the desired vinylsilane