101789-63-3Relevant articles and documents
Rh(I)-Catalyzed Decarboxylative Arylation of Alkynyl Cyclic Carbonates: Divergent Access to Substituted α-Allenols and 1,3-Butadienes
Sontakke, Geetanjali S.,Shukla, Rahul K.,Volla, Chandra M. R.
supporting information, p. 565 - 573 (2021/11/16)
Rh(I)-catalyzed decarboxylative arylation of alkynyl cyclic carbonates using commercially available and low-toxic aryl boronic acids has been disclosed. Depending on the nature of the cyclic carbonates, the methodology provides a straightforward platform to access either substituted 2,3-allenols or 1,3-butadiene derivatives. Internal alkynyl cyclic carbonates undergo monoarylation to conveniently afford 2,3-allenols with high syn-selectivity for the aryl and hydroxy groups. Whereas, terminal alkynyl carbonates led to the formation of diarylated 1,3-butadiene derivatives having cis-configuration for the two aryl groups via allenyl rhodium(I)alkoxide intermediate. The compatibility of various functional groups allowed to develop a library of diversely functionalized scaffolds with excellent regioselectivity in good yields. Late-stage transformation of a series of natural products highlights the wide applicability of the arylation process. Additionally, scale-up experiments and downstream transformations of α-allenol derivatives into other valuable heterocycles illustrate the efficacy of the protocol.
