Nickel‐Catalyzed CS Bond Formation: Synthesis of Aryl Sulfides from Arylsulfonyl Hydrazides and Boronic Acids

Abstract

A practical nickel‐catalysed approach has been developed for the CS bond formation through the cross‐coupling of arylsulfonyl hydrazides and aryl boronic acids. The report employs arylsulfonyl hydrazide as an aryl thiol equivalent and offers a mild and eco‐safe synthesis of unsymmetrical thioethers in good to excellent yields in air. The scope and versatility of the method has been successfully demonstrated with 22 examples.magnified image

Sulfonyl Hydrazides in Organic Synthesis: A Review of Recent Studies

“…Singh and Barman developed a new access to electrophilic RS‐DBU species in the presence of DBU (Eq. 59‐1).…”

Metal transition complexes of tridentate Schiff base ligands derived from 2-hydrazinopyridine: synthesis, spectroscopic characterization and X-ray structures

“…Although largely explored, the coordination chemistry of metal transition remains very interesting owing to the variably of the structures [1][2][3] and the possibility of applications in industries [4][5][6] of the complexes synthesized in this kind of chemistry. According to the metal center used, several degrees of oxidation, [7,8] different coordination numbers and original geometries that are not always easily predicted can be observed. The involvement of transition metal ions in various important biological processes [9][10][11], increases the interest of chemists in coordination chemistry.…”

Synthesis of aryl sulfides via radical–radical cross coupling of electron-rich arenes using visible light photoredox catalysis

“…Three of the five most selling drugs in 2015 were organosulfur compounds. The majority of methods for C–S bond synthesis use transition metal-catalyzed cross coupling of thiols and their derivatives with organohalides [ 4 – 6 ], arylboronic acids [ 7 ], aryl triflates [ 8 ], and diazonium salts [ 9 ]. Typical metals used are palladium [ 10 – 13 ], copper [ 14 – 21 ], nickel [ 22 – 24 ], iron [ 25 – 29 ], cobalt [ 30 – 32 ], and rhodium [ 33 – 34 ].…”