4.5 Article

Mono-N-Alkylation of Sulfonamides with Alcohols Catalyzed by Iridium N-Heterocyclic Carbene-Phosphine Complexes

Journal

ASIAN JOURNAL OF ORGANIC CHEMISTRY
Volume 11, Issue 7, Pages -

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/ajoc.202200178

Keywords

Alcohols; Borrowing hydrogenation; Iridium catalysis; N-alkylation; Sulfonamides

Funding

  1. Sichuan Science and Technology Program [2021YFH0161]
  2. National Natural Science Foundation of China [21811530004]
  3. Science and Technology Project of Southwest Petroleum University [2021JBGS07]
  4. Swedish Foundation for International Cooperation in Research and Higher Education [STINT CH2017-7226]
  5. Swedish research Council (VR)
  6. Knut and Alice Wallenberg foundation [KAW2016:0072, 2018:0066]
  7. Stiftelsen Olle Engkvist Byggmastare

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In this study, an efficient and selective mono-N-alkylation method for sulfonamides was developed based on a borrowing hydrogenation strategy. The use of water as the only by-product makes this method more environmentally friendly, and it shows good tolerance towards various types of sulfonamides and alcohols.
A N-heterocyclic carbene-phosphine iridium complex is presented for the efficient and selective mono-N-alkylation of sulfonamides with alcohols based on a borrowing hydrogenation strategy. Herein, water is the only by-product and this methodology thus offers a more environmentally benign and interesting alternative to the use of traditional alkylating reagents. This facile protocol tolerates a large number of (hetero) aromatic and aliphatic sulfonamides as well as (hetero) aromatic and aliphatic alcohols to obtain the desired product is high isolated yield (up to 98%). The alkylation completely retards after the formation of the secondary sulfonamide and no over-alkylation was observed in all cases. The option to run the reaction under solvent-free conditions as well as the scalability of this borrowing hydrogenation are key features of this protocol.

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