Palladium-catalyzed synthesis and nucleotide pyrophosphatase inhibition of benzo[4,5]furo[3,2-b]indoles

• Hoang Huy Do,
• Saif Ullah,
• Alexander Villinger,
• Joanna Lecka,
• Jean Sévigny,
• Peter Ehlers,
• Jamshed Iqbal and
• Peter Langer

Beilstein J. Org. Chem. 2019, 15, 2830–2839, doi:10.3762/bjoc.15.276

• studied double Buchwald–Hartwig reactions as the key step for the synthesis of heterocycles. For example, the cyclization of 2,2’-dibromobiaryls with amines allows for a convenient synthesis of carbazole derivatives [22][23][24][25][26][27][28][29][30]. Recently, we reported the synthesis of

Bromine–lithium exchange: An efficient tool in the modular construction of biaryl ligands

• Laurence Bonnafoux,
• Frédéric R. Leroux and
• Françoise Colobert

Beilstein J. Org. Chem. 2011, 7, 1278–1287, doi:10.3762/bjoc.7.148

• throughout the synthesis. Mixed dialkyl(diaryl)phosphinobiphenyls: Path B In order to synthesize mixed diphosphines, we took advantage of the non-equivalence of the two phenyl rings towards lithiation. We started from the same dibromobiaryls 1 as before, but submitted them now to just one equivalent of

• 2,2'-dibromobiaryls 1. A screening of the reaction conditions revealed higher yields for the double phosphination when the bromine–lithium exchange and trapping with ClPCy2 were carried out in toluene rather than in THF and at higher temperature. For example, with R1 = Me, OCF2O, and OCF2CF2O, the

Synthesis of unsymmetrically substituted biaryls via sequential lithiation of dibromobiaryls using integrated microflow systems

• Aiichiro Nagaki,
• Naofumi Takabayashi,
• Yutaka Tomida and
• Jun-ichi Yoshida

Beilstein J. Org. Chem. 2009, 5, No. 16, doi:10.3762/bjoc.5.16

• micromixers and microtube reactors provides an effective method for the introduction of two electrophiles onto dibromobiaryls. Selective monolithiation of dibromobiaryls, such as 2,2′-dibromobiphenyl, 4,4′-dibromobiphenyl, 2,7-dibromo-9,9-dioctylfluorene, 2,2′-dibromo-1,1′-binaphthyl, and 2,2′-dibromobibenzyl

• micromixers and four microtube reactors to obtain unsymmetrically substituted biaryl compounds. Keywords: dibromobiaryls; fast mixing; integrated microflow system; selective lithiation; unsymmetrically substituted biaryls; Introduction Unsymmetrical biaryls have received significant research interest

• ][53]. Recently, we reported that selective monolithiation can be achieved by extremely fast 1:1 micromixing of dibromobiaryls and n-butyllithium using microflow systems [54]. The successful results prompted us to perform a study on the synthesis of unsymmetrically substituted biaryls via sequential