Seyed Hashtroudi Mehri, Fathi Vavsari Vaezeh, Balalaie Saeed
Department of Ocean Sciences, Iranian National Institute for Oceanography and Atmospheric Science, Tehran, 1411813389, Iran.
Peptide Chemistry Research Institute, K. N. Toosi University of Technology, P. O. Box 15875-4416, Tehran, Iran.
Org Biomol Chem. 2022 Mar 16;20(11):2149-2163. doi: 10.1039/d1ob02199k.
1,4-Diazabicyclo[2.2.2]octane bis(sulfur dioxide), DABCO·SO, or DABSO, a bench-stable colorless solid, is industrially produced by the reaction of DABCO with condensed and bubbled sulfur dioxide gas at a low temperature. However, in some cases, it could catalyze organic reactions. DABSO is mostly used as a surrogate of gaseous sulfur dioxide to react with organic substrates, including Grignard reagents, aryl or alkyl halides, boronic acids, various amines, diazonium salts, carboxylic acids, heterocycles, acrylamides, alkenes, alkynes, and β-alkynyl ketones, through one-pot protocols, annulation, or coupling reactions. Most of these synthetic reactions proceed the formation of a sulfinate radical or anion. Using DABSO as a reagent, various simple to complex structures can be constructed, such as metal sulfinates, sulfonyl fluorides, sulfonamides, sulfonohydrazides, sulfonic esters, sulfonic thioesters, and sulfones. In this review, we want to investigate mechanistically the role of DABSO in organic synthesis.
1,4-二氮杂双环[2.2.2]辛烷双（二氧化硫），即DABCO·SO₂，或DABSO，是一种在实验室条件下稳定的无色固体，它是通过在低温下使DABCO与冷凝并鼓泡的二氧化硫气体反应而在工业上生产的。然而，在某些情况下，它可以催化有机反应。DABSO主要用作气态二氧化硫的替代物，通过一锅法、环化或偶联反应与有机底物反应，这些有机底物包括格氏试剂、芳基或烷基卤化物、硼酸、各种胺、重氮盐、羧酸、杂环、丙烯酰胺、烯烃、炔烃和β-炔基酮。这些合成反应大多通过形成亚磺酸盐自由基或阴离子进行。使用DABSO作为试剂，可以构建各种简单到复杂的结构，如金属亚磺酸盐、磺酰氟、磺酰胺、磺酰肼、磺酸酯、硫代磺酸酯和砜。在本综述中，我们希望从机理上研究DABSO在有机合成中的作用。
