38507-01-6Relevant academic research and scientific papers
Double C-H functionalization in sequential order: Direct synthesis of polycyclic compounds by a palladium-catalyzed C-H alkenylation-arylation cascade
Ohno, Hiroaki,Iuchi, Mutsumi,Kojima, Naoto,Yoshimitsu, Takehiko,Fujii, Nobutaka,Tanaka, Tetsuaki
supporting information; experimental part, p. 5352 - 5360 (2012/05/20)
Palladium-catalyzed cascade C-H alkenylation and arylation provides convenient access to polycyclic aromatic compounds. Treatment of 3-bromoaniline derivatives bearing a bromocinnamyl group on the nitrogen atom with a catalytic amount of [Pd(OAc)2] and PCy3aHBF4 in the presence of Cs2CO3 in dioxane affords naphthalene-fused indole derivatives in good yields. This double cyclization reaction is also applicable to heterocyclic substrates, giving fused indoles containing a heteroaromatic ring such as dibenzofuran, dibenzothiophene, carbazole, indole, or benzofuran through heterocyclic C-H arylation. When using a 2,6-unsubstituted aniline derivative, the first C-H arylation preferentially proceeds at the more hindered position of the aniline ring.
A highly stereoselective synthesis of (E)-α-bromoacrylates
Tago, Keiko,Kogen, Hiroshi
, p. 8825 - 8831 (2007/10/03)
Novel reagent, methyl bis(2,2,2-trifluoroethoxy)bromophosphonoacetate (5a), was designed and prepared in order to efficiently synthesize (E)-α-bromoacrylates 7, from which widely useful precursors for various C-C bond formations were prepared. Horner-Wadsworth-Emmons (HWE) reaction of various aldehydes with 5a in the presence of t-BuOK and 18-C-6 gave corresponding (E)-α-bromoacrylate derivatives with high stereoselectivity and excellent yield. Using the product (E)-α-bromoacrylate 7s as a key intermediate, we succeeded in developing the most effective route of plaunotol synthesis via Suzuki cross-coupling. (C) 2000 Elsevier Science Ltd.
