So far, in addition to halogen atoms, other non-metallic atoms can become part of the aromatic heterocycle, and the target ring system is still aromatic.Cho, Chang-Woo; Krische, Michael J. researched the compound: (R)-5,5′-Bis(diphenylphosphino)-2,2,2′,2′-tetrafluoro-4,4′-bi-1,3-benzodioxole( cas:503538-69-0 ).Computed Properties of C38H24F4O4P2.They published the article 《α-Hydroxy Esters via Enantioselective Hydrogen-Mediated C-C Coupling: Regiocontrolled Reactions of Silyl-Substituted 1,3-Diynes》 about this compound( cas:503538-69-0 ) in Organic Letters. Keywords: ester hydroxy preparation asym regioselective reductive coupling alkadiyne glyoxylate; coupling asym reductive alkadiyne oxo ester rhodium diphosphine catalyzed; enynoate hydroxy preparation asym regioselective coupling alkadiyne glyoxylate. We’ll tell you more about this compound (cas:503538-69-0).
Rhodium-catalyzed asym. reductive coupling of Et glyoxalate and 1,3-diynes in the presence of mol. hydrogen afforded α-hydroxy-β,γ-enynoates with high regio- and enantioselectivity. Reaction of R1CCCCR3 with OHCCOOR2 and H2 in the presence of Rh-(R)-Cl,MeO-BIPHEP [(1R)-5,5′-dichloro-6,6′-dimethoxy-1,1′-biphenyl-2,2′-bis(diphenylphosphine)] gave (2R)-R3CCCH:CR1CH(OH)COOR2 (1c, R1 = R3 = Ph, R2 = Et; 4c-9c, R1 = Me3Si, Me2tBuSi; R2 = Et; R3 = Ph, Me, cyclopropylmethyl, Me2tBuSiOCH2) with alkyne regioselectivity of >99% and ee values of 89-94%. Notably, for trialkylsilyl-substituted 1,3-diynes, C-C coupling occurs exclusively at the carbon atom bearing silyl group. π-Back-bonding from low valent rhodium as described by the Dewar-Chatt-Duncanson model appears to direct the regiochem. of C-C coupling, as corroborated by calculations of the diyne LUMO coefficients
In addition to the literature in the link below, there is a lot of literature about this compound((R)-5,5′-Bis(diphenylphosphino)-2,2,2′,2′-tetrafluoro-4,4′-bi-1,3-benzodioxole)Computed Properties of C38H24F4O4P2, illustrating the importance and wide applicability of this compound(503538-69-0).
Reference:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem