14293-06-2Relevant articles and documents
Direct photochemical cross-coupling between aliphatic acids and BF3K salts
Sun, Zhuming,Tang, Bingqing,Liu, Kevin K.-C.,Zhu, Hugh Y.
, p. 1294 - 1297 (2020)
We describe a novel photoredox hetero-coupling reaction of two C (sp3) radicals from aliphatic acids or BF3K salts. The kinetic differences in radical persistence provide cross-selectivity, using an organic photoredox catalyst and an oxidant with visible light. This method exhibits broad scope, including several examples constructing sterically hindered C(sp3)-C(sp3) bonds.
Photocatalytic α-Tertiary Amine Synthesis via C?H Alkylation of Unmasked Primary Amines
Alder, Catherine M.,Ballantyne, George,Cresswell, Alexander J.,Cunningham, William B.,Edwards, Lee J.,Grayson, Matthew N.,Kinsella, Anna G.,McKay, Blandine S. J.,Mules, Tom,Ryder, Alison S. H.,Turner-Dore, Jacob
, p. 14986 - 14991 (2020/06/20)
A practical, catalytic entry to α,α,α-trisubstituted (α-tertiary) primary amines by C?H functionalisation has long been recognised as a critical gap in the synthetic toolbox. We report a simple and scalable solution to this problem that does not require any in situ protection of the amino group and proceeds with 100 percent atom-economy. Our strategy, which uses an organic photocatalyst in combination with azide ion as a hydrogen atom transfer (HAT) catalyst, provides a direct synthesis of α-tertiary amines, or their corresponding γ-lactams. We anticipate that this methodology will inspire new retrosynthetic disconnections for substituted amine derivatives in organic synthesis, and particularly for challenging α-tertiary primary amines.
Strategic Approach to the Metamorphosis of γ-Lactones to NH γ-Lactams via Reductive Cleavage and C-H Amidation
Jung, Hoi-Yun,Chang, Sukbok,Hong, Sungwoo
, p. 7099 - 7103 (2019/09/07)
A new approach has elaborated on the conversion of γ-lactones to the corresponding NH γ-lactams that can serve as γ-lactone bioisosteres. This approach consists of reductive C-O cleavage and an Ir-catalyzed C-H amidation, offering a powerful synthetic tool for accessing a wide range of valuable NH γ-lactam building blocks starting from γ-lactones. The synthetic utility was further demonstrated by the late-stage transformation of complex bioactive molecules and the asymmetric transformation.
