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

Li, Xingzhen (author)
Peters, Bram B. C. (author)
Stockholms universitet,Institutionen för organisk kemi
Tan, Min (author)
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He, Lei (author)
Yang, Jianping (author)
Stockholms universitet,Institutionen för organisk kemi
Andersson, Pher G. (author)
Stockholms universitet,Institutionen för organisk kemi,University of Kwazulu-Natal, South Africa
Zhou, Taigang (author)
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 (creator_code:org_t)
2022-06-21
2022
English.
In: Asian Journal of Organic Chemistry. - : Wiley. - 2193-5807 .- 2193-5815. ; 11:7
  • Journal article (peer-reviewed)
Abstract Subject headings
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  • 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.

Subject headings

NATURVETENSKAP  -- Kemi (hsv//swe)
NATURAL SCIENCES  -- Chemical Sciences (hsv//eng)

Keyword

Alcohols
Borrowing hydrogenation
Iridium catalysis
N-alkylation
Sulfonamides

Publication and Content Type

ref (subject category)
art (subject category)

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