Mn(OAc)3-promoted regioselective free radical thiocyanation of indoles and anilines

Green Thiocyanation of Aromatic and Heteroaromatic Compounds by Using Silica Boron Sulfonic Acid as a New Catalyst and H<SUB>2</SUB>O<SUB>2</SUB> as Mild Oxidant

“…The addition was highly regioselective occurring at the 3-position of the indole ring. 19,37 Various N,N-disubstituted aromatic amines were converted into the respective 4-thiocyanato amine in high to excellent overall yields ( Table 2, entries 5-10). The reactions were clean and the products were obtained with high para-selectivity (Table 2, entry 9, 10).…”

An Efficient Selectfluor-Mediated Oxidative Thio- and Selenocyanation of Diversely Substituted Indoles and Carbazoles

“…Aryl thio-and selenocyanates are versatile intermediates for various sulfur-and selenium-containing compounds that are of synthetic and biological interest [14][15][16][17][18][19][20][21][22][23][24][25][26]. Aryl thiocyanates are widely employed as building blocks in the synthesis of diverse sulfides [27,28], thiocarbamates [29], thionitriles [30], sulfonic acids [31], sulfonyl chlorides [32], thioesters [33], and sulfonyl cyanides [31] and mainly in the synthesis and functionalization of heterocyclic compounds [25,26,[34][35][36][37][38][39][40].…”

“…Owing to the aforementioned chemical versatility and biological activity, functional organic compounds bearing the thiocyanato and selenocyanate derivatives are highly sought after, and over the years a number of strategies and reagents have been utilized to enable the direct introduction of SCN and SeCN moieties into organic motifs. In particular, direct oxidative thiocyanation of C-H bonds have been achieved by using thiocyanate salts in the presence of oxidizing agents such as Mn(OAc) 3 [15], NCS [47], CAN [48], hypervalent iodine reagents [49], DDQ [50], oxone [51], oxygen [52], DEAD [53], and TBHP [22]. In comparison, direct selenocyanation approaches have not been reported under similar oxidative conditions [20][21][22][23][24][25][26].…”

Quinolinium bound chromium(VI) reagents for efficient electrophilic aromatic nitration and thiocyanation reactions using sodium nitrate and ammonium thiocyanate

“…The unspent acids left out in these protocols often cause environmental pollution. In recent years, several new approaches have been developed to control the regiochemistry of the reactions [3][4][5][6][7][8][9][10][11][12][13][14][15][16][17][18][19][20].…”