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- Title
Metal-free photoinduced C(sp<sup>3</sup>)–H/C(sp<sup>3</sup>)–H cross-coupling to access α‑tertiary amino acid derivatives.
- Authors
Li, Yujun; Guo, Shaopeng; Li, Qing-Han; Zheng, Ke
- Abstract
The cross-dehydrogenative coupling (CDC) reaction is the most direct and efficient method for constructing α-tertiary amino acids (ATAAs), which avoids the pre-activation of C(sp3)-H substrates. However, the use of transition metals and harsh reaction conditions are still significant challenges for these reactions that urgently require solutions. This paper presents a mild, metal-free CDC reaction for the construction of ATAAs, which is compatible with various benzyl C-H substrates, functionalized C-H substrates, and alkyl substrates, with good regioselectivity. Notably, our method exhibits excellent functional group tolerance and late-stage applicability. According to mechanistic studies, the one-step synthesized and bench-stable N-alkoxyphtalimide generates a highly electrophilic trifluoro ethoxy radical that serves as a key intermediate in the reaction process and acts as a hydrogen atom transfer reagent. Therefore, our metal-free and additive-free method offers a promising strategy for the synthesis of ATAAs under mild conditions. The cross-dehydrogenative coupling (CDC) reaction is the most efficient method for constructing α-tertiary amino acids (ATAAs). Here, the authors present a mild, metal-free CDC reaction for the construction of ATAAs with good regioselectivity.
- Subjects
AMINO acid derivatives; ABSTRACTION reactions; FUNCTIONAL groups; TRANSITION metals; RADICALS (Chemistry); AMINO acids
- Publication
Nature Communications, 2023, Vol 14, Issue 1, p1
- ISSN
2041-1723
- Publication type
Article
- DOI
10.1038/s41467-023-41956-6