Synlett 2020; 31(08): 772-783
DOI: 10.1055/s-0039-1690815
account
© Georg Thieme Verlag Stuttgart · New York

Reactions Catalyzed by 2-Halogenated Azolium Salts: From Halogen-Bond Donors to Brønsted-Acidic Salts

,
This work was partly supported by the Japan Society for the Promotion of Science (JSPS) (KAKENHI) (Grant Nos. 16H06384, 17K15423 and 19K06974) as well as by the Japan Agency for Medical Research and Development (AMED), Platform Project for Supporting Drug Discovery and Life Science Research [Basis for Supporting Innovative Drug Discovery and Life Science Research (BINDS)] (Grant No. JP19am0101092j0003). Y.K. also thanks the Takeda Science Foundation.
Further Information

Publication History

Received: 26 December 2019

Accepted after revision: 17 January 2020

Publication Date:
06 February 2020 (online)


Abstract

Our research group has developed a variety of organocatalysts, especially bi- and multi-functional hydrogen-bond (HB)-donor catalysts. Since 2013, we have become interested in halogen-bond (XB) interactions in organic synthesis, and we have focused on the development of organocatalysts using XBs. Although it is difficult to develop otherwise inaccessible transformations using XBs as the primary interaction, we found several unique reactions that use XB interactions in combination with co-catalysts such as trimethylsilyl iodide, Proton Sponge, and Schreiner’s thiourea. During the synthesis of various 2-iodoazolium salts that can serve as XB donors, a ‘protonated’ 2-iodoazolium salt (a Brønsted-acidic salt) was unexpectedly obtained instead of the corresponding ‘alkylated’ 2-iodoazolium salt (XB donor). The obtained Brønsted-acidic salt is unprecedentedly effective for the N-glycosylation of amides. This account summarizes our findings in this area to date.

1 Introduction

2 Organoiodine-Compound-Mediated Semipinacol Rearrangement via C–X Bond Cleavage

3 2-Iodoazolium-Salt-Catalyzed Reactions through Halogen Bonding (XB)

3.1 TMSI-Co-catalyzed Dehydroxylative Coupling of Alcohols with ­Organosilanes

3.2 Base-Co-catalyzed Umpolung Alkylation of Oxindoles with an ­Iodonium(III) Ylide

3.3 Thiourea-Co-catalyzed N-Glycofunctionalization of Amides

3.4 Thiourea-Co-catalyzed N-α-Glycosylation of Amides

4 Catalytic Reactions Using 2-Haloazolium Salts as the Brønsted Acids

4.1 N-β-Glycosylation of Amides

4.2 N-β-2-Deoxyglycosylation of Amides

5 Conclusions

 
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