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Abstract Toxic organic solvents and electrolytes, traditionally indispensable for electro‐organic synthesis, are now being reconsidered. In developing more sustainable electro‐organic synthesis, we've harnessed the aqueous micelles as solvents and electrolyte‐like structures when deformed under an electric field. The technology is showcased in synthetically highly valued hydrodefluorination reactions of difluorinated indoles. This mild electrosynthetic method produces monofluorinated unprotected indole scaffolds. Our approach minimizes waste and enhances atom economy, reducing reliance on expensive and hazardous solvents and electrolytes. The surfactant's potential for recycling was verified for two cycles. Cyclic voltammetry analysis has corroborated that PS‐750‐M micelles in water establish a more efficient platform for hydrodefluorination. Our technology simplifies the production of monofluorinated indoles, which are crucial for many drug‐like molecules.
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Regioselective Formation of Substituted Indoles: Formal Synthesis of Lysergic Acid
Abstract A Diels–Alder reaction‐based strategy for the synthesis of indoles and related heterocycles is reported. An intramolecular cycloaddition of alkyne‐tethered 3‐aminopyrones gives 4‐substituted indolines in good yield and with complete regioselectivity. Additional substitution is readily tolerated in the transformation, allowing synthesis of complex and non‐canonical substitution patterns. Oxidative conditions give the corresponding indoles. The strategy also allows the synthesis of carbazoles. The method was showcased in a formal synthesis of lysergic acid.
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- Award ID(s):
- 1956401
- PAR ID:
- 10236171
- Publisher / Repository:
- Wiley Blackwell (John Wiley & Sons)
- Date Published:
- Journal Name:
- Chemistry – A European Journal
- Volume:
- 26
- Issue:
- 70
- ISSN:
- 0947-6539
- Format(s):
- Medium: X Size: p. 16655-16658
- Size(s):
- p. 16655-16658
- Sponsoring Org:
- National Science Foundation
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