2008
DOI: 10.1002/anie.200803213
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Palladium‐Catalyzed Annulation of vic‐Bis(pinacolatoboryl)alkenes and ‐phenanthrenes with 2,2′‐Dibromobiaryls: Facile Synthesis of Functionalized Phenanthrenes and Dibenzo[g,p]chrysenes

Abstract: Double‐cross: An annulation approach to functionalized polycyclic aromatic hydrocarbons involving a palladium‐catalyzed double cross‐coupling reaction of vic‐diborylalkenes and ‐phenanthrenes with 2,2′‐dibromobiaryls led to a variety of phenanthrenes and dibenzo[g,p]chrysenes, as well as [5]helicenes, dithienobenzenes, and triphenyleno[1,2‐b:4,3‐b′]dithiophenes (see scheme; Bpin=pinacolatoboryl).

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Cited by 133 publications
(44 citation statements)
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“…After concentration in vacuo, purification by flash column chromatography on silica gel (eluent: n ‐hexane) afforded the title compound ( 2 , 30 mg, 89 %) as a colorless solid. Analytical data were in good accordance with data reported in the literature 10a…”
Section: Methodssupporting
confidence: 89%
“…After concentration in vacuo, purification by flash column chromatography on silica gel (eluent: n ‐hexane) afforded the title compound ( 2 , 30 mg, 89 %) as a colorless solid. Analytical data were in good accordance with data reported in the literature 10a…”
Section: Methodssupporting
confidence: 89%
“…Thec arboxylic acid group not only serves as al eaving group in decarboxylative reactions,b ut can be employed as ad irecting group in cross-coupling reactions. [10] Heteroarenes are key structural motifs in av ariety of natural products and biologically active compounds.F or instance,f unctionalized fused furan derivatives represent an elegant class of Oheterocycles with wide range of applications in pharmaceuticals and agrochemicals research. [8] Decarboxylative annulation reactions have recently been studied comprehensively for the synthesis of polynuclear aromatic hydrocarbons [8b, 9] and heteroarenes.…”
mentioning
confidence: 99%
“…of MPHT ( Table 2, Entries 1 and 2). We were pleased to observe the quantitative formation of bis(3-bromobenzofuran) 4a and bis(3-bromobenzothiophene) 4b, which were used as starting materials for the synthesis of benzannulated phospholes, [15] dibenzothienopyrroles, [16] dithienosiloles, [17] and functionalized phenanthrenes [18] of physical interest. Unsymmetrical diyne 3c reacted cleanly with MPHT to afford expected heterocycle 4c, again with excellent yield (Table 2, Entry 3).…”
Section: Resultsmentioning
confidence: 99%