59734-91-7Relevant academic research and scientific papers
Modular Generation of (Iodinated) Polyarenes Using Triethylgermane as Orthogonal Masking Group
Deckers, Kristina,Fricke, Christoph,Hupperich, Daniel,Kreisel, Tatjana,Mendel, Marvin,Queen, Adele E.,Riegger, Julian,Schoenebeck, Franziska
, (2022/03/31)
While the modular construction of molecules from suitable building blocks is a powerful means to more rapidly generate a diversity of molecules than through customized syntheses, the further evolution of the underlying coupling methodology is key to realize widespread applications. We herein disclose a complementary modular coupling approach to the widely employed Suzuki coupling strategy of boron containing precursors, which relies on organogermane containing building blocks as key orthogonal functionality and an electrophilic (rather than nucleophilic) unmasking event paired with air-stable PdI dimer based bond construction. This allows to significantly shorten the reaction times for the iterative coupling steps and/or to close gaps in the accessible compound space, enabling straightforward access also to iodinated compounds.
Bioinspired Metal-Free Formal Decarbonylation of α-Branched Aliphatic Aldehydes at Ambient Temperature
Richter, Sven C.,Oestreich, Martin
, p. 8508 - 8512 (2019/06/04)
A sequence of a Baeyer–Villiger oxidation and a Lewis acid-promoted reduction of the resulting formate with Et3SiH enabled the metal-free formal decarbonylation of tertiary and secondary aliphatic aldehydes. The new methodology mimics the biosynthetic decarbonylation pathway through oxidative C?C bond cleavage rather than the C(O)?H bond activation known from conventional Tsuji–Wilkinson-type reactions. The substrate scope is complementary to existing transition-metal-catalyzed protocols.
Nickel-Catalyzed Cross-Coupling of Redox-Active Esters with Boronic Acids
Wang, Jie,Qin, Tian,Chen, Tie-Gen,Wimmer, Laurin,Edwards, Jacob T.,Cornella, Josep,Vokits, Benjamin,Shaw, Scott A.,Baran, Phil S.
supporting information, p. 9676 - 9679 (2016/08/10)
A transformation analogous in simplicity and functional group tolerance to the venerable Suzuki cross-coupling between alkyl-carboxylic acids and boronic acids is described. This Ni-catalyzed reaction relies upon the activation of alkyl carboxylic acids as their redox-active ester derivatives, specifically N-hydroxy-tetrachlorophthalimide (TCNHPI), and proceeds in a practical and scalable fashion. The inexpensive nature of the reaction components (NiCl2?6 H2O—$9.5 mol?1, Et3N) coupled to the virtually unlimited commercial catalog of available starting materials bodes well for its rapid adoption.
