Nickel-induced conversion of carbon–sulphur into carbon–carbon bonds. One-step transformations of enol sulphides into olefins and benzenethiol derivatives into alkylarenes and biaryls

Palladium-catalyzed desulfinylative C–C allylation of Grignard reagents and enolates using allylsulfonyl chlorides and esters

“…29 We have also shown that aliphatic sulfonyl chlorides are also excellent electrophiles. 31 Among the earliest, most economical and useful nucleophilic partners are the Grignard reagents, which can be coupled with all kinds of electrophilic partners such as sulfides, [32][33][34][35][36][37][38][39] sulfoxides 32,40 sulfoximines, [41][42][43][44][45] sulfones, 46-52 sulfonic esters, [53][54][55] and sulfonamides 56 in the presence of nickel catalysts.…”

Nickel‐ or Cobalt‐Catalyzed Cross‐Coupling of Arylsulfonic Acid Salts with Grignard Reagents

“…Phenol-derivede lectrophiles,i ncluding phenolic salts, [2] sulfonates, [3] sulfates, [4] phosphates, [5] ethers, [6] esters, [7] carbamates, [8] carbonates, [8b] and sulfamates [8a-b,9] have been shown to be competent C À O electrophiles in manyt ypes of cross-coupling reactions.A rylamine derivatives such as diazonium salts, [10] trimethylammonium salts, [11] triazenes, [12] and even anilines [13] have been developed as C À Nb ased electrophiles.T he use of aryl-sulfur derivatives as electrophiles was pioneered by Wenkert andc o-workers in 1979, when they extended their work on the Nicatalyzed coupling of vinyl anda ryl ethers with Grignard reagents [6a] to the analogous cross-coupling of vinyl sulfides,a ryl thiols,a ryl sulfides,a ryl sulfoxides,a ryl sulfones,a nd arylsulfinate salts with Grignard reagents. [14] Theu se of aryl tert-butyl sulfones (Julia andc o-workers), [15] neopentyl arylsulfonates (Park and co-workers), [16] and N,N-diethylarylsulfonamides (Snieckus and co-workers) [17] was subsequently reported for Ni-catalyzed cross-coupling with Grignard reagents.V ogel and co-workers have developed several desulfinylative cross-coupling reactions with arylsulfonylc hloridesa st he electrophiles. [18] Aryl-sulfur electrophiles have shown compatibility with an array of different transitionm etal-catalyzed cross-coupling reactions.…”

Cross-Coupling Reactions Catalyzed by Iron Group Metals and <i>N</i>-Heterocyclic Carbenes via Nonconventional Reaction Mechanisms

“…Despite a long history starting with independent publications by Wenkert 58 and Takei 59 in 1979, organosulfur compounds 60 have received far less attention as electrophilic substrates in cross coupling chemistry than other substrates, such as halides, sulfonates, and phosphates. The underuse of organosulfur compounds is partly due to their malodorous smell 61 and the perception that they are a lesser substitute for other electrophiles.…”