Abstract Sulfur dioxide has a rich and varied chemistry that can be traced back to the early 1900s. Despite potential utility of sulfur based reactions, delivering products such as sulfones, sulfonamides sulfinic acids, number examples these reactions being exploited in synthesis is arguably lower than would expected. One significant contributing factor this undoubtedly toxic gaseous nature SO 2 . strategy overcome limitation employ an equivalent, or surrogate, so reagent no longer needed....

The palladium-catalyzed three-component coupling of aryl iodides, sulfur dioxide, and hydrazines to deliver N-aminosulfonamides is described. colorless crystalline solid DABCO·(SO(2))(2) was used as a convenient source dioxide. reaction tolerates significant variation both the iodide hydrazine partners.

The charge-transfer complex generated from the combination of DABCO and sulfur dioxide, DABSO, is a bench-stable colorless solid suitable for use in organic synthesis as replacement gaseous dioxide. can be combined with Grignard reagents to form sulfinates, which then converted situ series sulfonamides. Alternatively, reaction anilines iodine leads formation sulfamides. Cheletropic addition between DABSO 2,3-dimethylbutadiene provides corresponding sulfolene.

SO(2) efficient: A three-component palladium-catalyzed coupling of aryl lithium compounds; sulfur dioxide (provided by the easy-to-handle solid surrogate, DABSO); and aryl, heteroaryl, alkenyl (pseudo)halides yields a diverse library sulfones. An electron-poor XantPhos-type ligand suppresses aryl–aryl exchange is key to obtaining high yields.

Abstract A redox‐neutral palladium(II)‐catalyzed conversion of aryl, heteroaryl, and alkenyl boronic acids into sulfinate intermediates, onwards to sulfones sulfonamides, has been realized. simple Pd(OAc) 2 catalyst, in combination with the sulfur dioxide surrogate 1,4‐diazabicyclo[2.2.2]octane bis(sulfur dioxide) (DABSO), is sufficient achieve rapid high‐yielding corresponding sulfinates. Addition C‐ or N‐based electrophiles then allows respectively, a one‐pot, two‐step process.

Sulfonyl-derived functional groups populate a broad range of useful molecules and materials, despite variety preparative methods being available, processes which introduce the most basic sulfonyl building block, sulfur dioxide, using catalytic methods, are rare. Described herein is simple reaction system consisting dioxide surrogate DABSO, triethylamine, palladium(0) catalyst for effective convertion aryl heteroaryl halides into corresponding ammonium sulfinates. Key features this gas-...

A mild, efficient synthesis of sulfonyl fluorides from aryl and heteroaryl bromides utilizing palladium catalysis is described.

First introduced into medicines in the 1930s, sulfonamide functional group continues to be present a wide range of contemporary pharmaceuticals and agrochemicals. Despite their popularity design modern bioactive molecules, underpinning methods for synthesis are essentially unchanged since introduction, rely on use starting materials with preinstalled sulfur-functionality. Herein we report direct single-step sulfonamides that combines two largest monomer sets available discovery chemistry,...

M. C. Willis, J. Chem. Soc., Perkin Trans. 1, 1999, 1765 DOI: 10.1039/A906269B

The scope of highly enantioselective and diastereoselective Michael additions enolsilanes to unsaturated imide derivatives has been developed with use [Cu((S,S)-t-Bu-box)](SbF6)2 (1a) as a Lewis acid catalyst. products these are useful synthons that contain termini capable differentiation under mild conditions. acceptor π-facial selectivity is consistent two-point binding the substrate can be viewed an extension enantioselection in corresponding Diels−Alder reactions. A model analogous one...

The addition of Grignard reagents or organolithium to the SO2-surrogate DABSO generates a diverse set metal sulfinates, suitable for direct conversion sulfone products. sulfinates can be trapped in situ with wide range C-electrophiles, including alkyl, allyl, and benzyl halides, epoxides, (hetero)aryliodoniums.

A single tandem operation allows rapid access to a variety of substituted N-functionalized indoles. The nitrogen atom the indole nucleus is incorporated through Pd-catalyzed aryl and alkenyl CN bond-forming reactions (see scheme; dba=dibenzylideneacetone). Amine, aniline, amide, carbamate, sulfonamide functional groups can be introduced efficiently.

5-Iodouracil-substituted RNA and DNA were crosslinked regiospecifically to associated proteins in yields of 70 94% bound nucleic acid. Irradiation the iodouracil chromophore with monochromatic, long-wavelength ultraviolet radiation (325 nanometers) eliminates excitation other acid protein chromophores. The combination high crosslinking yields, excellent specificity, elimination photodamage chromophores represents an important advance toward precise identification contacts nucleoprotein complexes.

Back to basics: Ligand design has allowed two longstanding limitations of Pd-catalyzed CN and CO coupling reactions be overcome. The use specific sterically demanding electron-rich phosphine ligands makes it possible for ammonia potassium hydroxide act as partners in palladium-catalyzed with aryl halides. last decade seen the bond-forming cross-coupling halides emerge tremendously powerful synthetic tools.1 Both processes have reached a level sophistication that allows wide range combined...

A rhodium(I) catalyst incorporating the Me-DuPhos ligand promotes enantioselective intermolecular hydroacylation between beta-S-aldehydes and 1,3-disubstituted allenes. The nonconjugated enone products are obtained in good yields with high enantioselectivities.

Abstract We describe a method for the synthesis of sulfonamides through combination an organometallic reagent, sulfur dioxide equivalent, and aqueous solution amine under oxidative conditions (bleach). This simple reaction protocol avoids need to employ sulfonyl chloride substrates, thus removing limitation imposed by commercial availability these reagents. The resultant allows access new chemical space, is also tolerant polar functional groups needed impart favorable physiochemical...

The recent development of several sulfur dioxide surrogates has seen a renaissance in its chemistry, with number new synthetic methods being reported. This article reviews the reactions and surrogates, an emphasis on examples. 1 Introduction 2 Sulfur Dioxide Surrogates 3 Reactions Organometallic Reagents 4 Pericyclic 5 Radical Chemistry 6 Transition-Metal-Catalysed Processes 7 Conclusions

A sulfonylative variant of a “classic” cross-coupling, with broad substrate scope. The electrophilic trapping sulfinate intermediate was also possible.

A Rh(I)-catalyzed method for the efficient functionalization of arenes is reported. Aryl methyl sulfides are combined with terminal alkynes to deliver products carbothiolation. The overall process results in reincorporation original arene functional group, a sulfide, into as an alkenyl sulfide. carbothiolation can be initial alkene or alkyne hydroacylation reaction three-component cascade sequences. utility sulfide also demonstrated simple carbo- and heterocycle-forming processes. We provide...

A palladium-catalysed aminosulfonylation process is used as the key-step in a one-pot, three-component sulfone synthesis. The combines aryl-, heteroaryl- and alkenyl iodides with sulfonyl unit an electrophilic coupling fragment. delivered form of aminosulfonamide, which then serves masked sulfinate. sulfinate combined, situ, partner, such benzylic, allylic or alkyl halide, electron-poor arene, cyclic epoxide, to provide corresponding products good excellent yields. mild reaction conditions...