DABSO – A Reagent to Revolutionize Organosulfur Chemistry

Abstract

The introduction of easy-to-handle SO2 surrogates has transformed the field of sulfur chemistry, enabling methodologies utilizing SO2 to be carried out without specialized apparatus, and paving the way for the development of new procedures. This review highlights some of the varied and significant developments associated with one of the most prominent SO2 surrogates: DABSO.1 Introduction2 DABSO3 Reactions with Nucleophilic Reagents4 Metal-Catalyzed Reactions4.1 Palladium-Catalyzed Reactions4.2 Other Transition-Metal Catalysis5 Radical Reactions5.1 Aryldiazonium Salts5.2 Other Aryl Radical Precursors5.3 Alkyl Radical Precursors6 Conclusion

Visible‐Light Induced Fixation of SO2 into Organic Molecules with Polypyridine Chromium(III) Complexes

“…[17] The introduction of easy-to-handle surrogates for the toxic and corrosive SO 2 gas, such as the 1,4-diazabicyclo[2.2.2]octane (DABCO)-sulfur dioxide adduct DABSO, has been a major driving force in this field. [18][19][20] Yet, the stoichiometric release of DABCO mitigates atom economy and may pose other concerns such as side reactions.…”

“…Compared to traditional methods, [16] these novel processes enable highly modular and inherently more sustainable synthesis of sulfones or sulfonamides utilizing SO 2 as key building block [17] . The introduction of easy‐to‐handle surrogates for the toxic and corrosive SO 2 gas, such as the 1,4‐diazabicyclo[2.2.2]octane (DABCO)‐sulfur dioxide adduct DABSO, has been a major driving force in this field [18–20] . Yet, the stoichiometric release of DABCO mitigates atom economy and may pose other concerns such as side reactions.…”

A palladium-catalyzed cross-electrophile coupling reaction involving sulfur dioxide for the direct synthesis of diversely functionalized sulfones

“…9 However, these strategies employ poorly accessible sulfur-containing starting materials and therefore have limited applicability. Recently, substantial effort has been made for the development of sulfur dioxide (SO 2 ) insertion reactions, 10 which could rapidly generate sulfonyl compounds from readily available substrates. To avoid the inconvenient two-step operation, 11 one-step construction of sulfones from various organometallic reagents 12 ( e.g.…”

Visible-light promoted cascade cyanoalkylsulfonylation/ipso-cyclization ofN-arylpropiolamides toward sulfonated spiro[4,5]trienonesviaSO2insertion

“…This strategy provides a safe and easy-to-handle protocol to synthesize sulfones under mild conditions without using the toxic and corrosive SO 2 gas. 6…”