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Alkylation of

Cayden J Dodd1, Daniel C Schultz1, Jinming Li1

  • 1Warren Center for Neuroscience Drug Discovery, Department of Pharmacology, Vanderbilt University, 393 Nichol Mill Lane, Franklin, TN, 37067, USA. aaron.bender@vanderbilt.edu.

Organic & Biomolecular Chemistry
|June 9, 2023
PubMed
Summary
This summary is machine-generated.

This study presents a new, simple method for alkylating NH-sulfoximines using Mitsunobu-type conditions. This approach avoids harsh reagents and transition metals, offering a more accessible route for chemical synthesis.

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Area of Science:

  • Organic Chemistry
  • Synthetic Chemistry

Background:

  • Traditional NH-sulfoximine alkylation often requires transition metal catalysts or strong bases.
  • These methods can be limited by substrate scope and harsh reaction conditions.

Purpose of the Study:

  • To develop a straightforward and mild method for the alkylation of NH-sulfoximines.
  • To demonstrate the broad applicability of this new method to diverse NH-sulfoximine substrates.

Main Methods:

  • The study employed Mitsunobu-type reaction conditions.
  • A variety of NH-sulfoximines were reacted with different alkylating agents.

Main Results:

  • A straightforward alkylation of diverse NH-sulfoximines was achieved.
  • The reaction proceeded efficiently under mild Mitsunobu-type conditions.
  • This method is effective despite the high pKa of the NH center in sulfoximines.

Conclusions:

  • A novel and accessible Mitsunobu-type alkylation of NH-sulfoximines has been established.
  • This method offers an alternative to traditional, harsher alkylation techniques.
  • The developed protocol broadens the synthetic utility of NH-sulfoximines.