1040745-70-7Relevant articles and documents
Manganese(III)-Promoted Double Carbonylation of Anilines Toward α-Ketoamides Synthesis
Chen, Bo,Kuai, Chang-Sheng,Xu, Jian-Xing,Wu, Xiao-Feng
supporting information, p. 487 - 492 (2021/12/06)
Employing anilines as nucleophiles in double carbonylation is a longstanding challenge. In this communication, a Mn(III)-promoted double carbonylation of alkylborates or Hantzsch esters with anilines toward the synthesis of α-ketoamides has been developed. By using easily available potassium alkyltrifluoroborates or Hantzsch esters as the starting material, and cheap and non-toxic Mn(OAc)3 ? 2H2O as the promotor, a broad range of alkyl α-ketoamide derivatives were synthesized in moderate to good yields with excellent selectivity. (Figure presented.).
Visible-Light-Induced C2 Alkylation of Pyridine N-Oxides
Zhang, Wen-Man,Dai, Jian-Jun,Xu, Jun,Xu, Hua-Jian
, p. 2059 - 2066 (2017/02/26)
A photoredox catalytic method has been developed for the direct C2 alkylation of pyridine N-oxides. This reaction is compatible with a range of synthetically relevant functional groups for providing efficient synthesis of a variety of C2-alkylated pyridine N-oxides under mild conditions. Mechanistic studies are consistent with the generation of a radical intermediate along the reaction pathway.
Synergistic Photoredox/Nickel Coupling of Acyl Chlorides with Secondary Alkyltrifluoroborates: Dialkyl Ketone Synthesis
Amani, Javad,Molander, Gary A.
, p. 1856 - 1863 (2017/02/10)
Visible light photoredox/nickel dual catalysis has been employed in the cross-coupling of acyl chlorides with potassium alkyltrifluoroborates. This protocol, based on single-electron-mediated alkyl transfer, circumvents the restriction of using reactive alkylmetallic nucleophiles in transition-metal-catalyzed acylation and achieves a mild and efficient method for the synthesis of unsymmetrical alkyl ketones. In this approach, a variety of acyl chlorides have been successfully coupled with structurally diverse potassium alkyltrifluoroborates, generating the corresponding ketones with good yields.
Decarboxylative Borylation of Aliphatic Esters under Visible-Light Photoredox Conditions
Hu, Dawei,Wang, Linghua,Li, Pengfei
supporting information, p. 2770 - 2773 (2017/05/24)
The conventional methods for preparing alkyl boronates often necessitate anhydrous and demanding reaction conditions. Herein, a new, operationally simple decarboxylative borylation reaction of readily available aliphatic acid derivatives under additive-free visible-light photoredox conditions in nonanhydrous solvents has been described. Primary and secondary alkyl boronates or tetrafluoroborates with various functional groups were prepared accordingly. A catalytic cycle involving alkyl radical reaction with base-activated diboron species has been proposed.
Efficient cross-coupling of secondary alkyltrifluoroborates with aryl chlorides-reaction discovery using parallel microscale experimentation
Dreher, Spencer D.,Dormer, Peter G.,Sandrock, Deidre L.,Molander, Gary A.
supporting information; body text, p. 9257 - 9259 (2009/02/02)
Microscale parallel experimentation was used to discover three catalyst systems capable of coupling secondary organotrifluoroborates with sterically and electronically demanding aryl chlorides and bromides. The ensuing results represent the first comprehensive study of alkylboron coupling to aryl chlorides and, in particular, using secondary alkylboron partners. A ligand-dependent β-hydride elimination/reinsertion mechanism was implicated in the cross-coupling of more hindered substrates, leading to isomeric mixtures of coupled products in some cases. Copyright
