Direct alkenylation of alkylazaarenes with aldehydes through C(sp3)–H functionalization under catalytic InCl3 activation

Recent synthetic efforts in the preparation of 2-(3,4)-alkenyl (aryl) quinoline molecules towards anti-kinetoplastid agents

“…Thus, nowadays acid-catalysed reactions of 2-methylquinolines and aldehydes have become very popular. Wang group reported La(P) 3 -catalysed reaction of 2-methylquinolines 3 and benzaldehydes 15 in boiling toluene (120 C, air, 24 h) to prepare styrylquinolines 18 in good to excellent yields (55-99%), 72 while Teo and co-workers described catalytic InCl 3 (10 mol%) and CoCl 2 (10 mol%) activation (THF, 120 C, 24 h) of this type of reaction 73,74 and Yaragorla group realized this reaction heating them in closed vessel at 130 C for 4-5 h in the presence of Ca(OTf) 2 (5 mol%) and Bu 4 NPF 6 (2 mol%). 75 Russian researchers also reported the synthesis of 2-styrylquinoline derivatives 18 under microwave irradiation in the presence of zinc chloride (Table 3).…”

NH4I-mediated sp3 C-H cross-dehydrogenative coupling of benzylamines with 2-methylquinoline for the synthesis of E-2-styrylquinolines

“…8 The wide applications of E-2styrylquinolines have attracted considerable attention in synthetic chemistry. In the past 10 years, widely used methods for the synthesis of E-2-styrylquinolines have mainly involved the reactions of 2-methylquinolines with benzyl alcohols, [9][10][11][12] benzyl amines, 9,[13][14][15] aldehydes, [16][17][18][19] and N-benzylidene-4-methylbenzenesulfonamides 20 (Scheme 1). In 2011, Qian et al 20 disclosed that Fe(OAc) 2 promoted the reactions of 2-methylquinolines and N-benzylidene-4-methylbenzenesulfonamides by removing a molecule of p-toluenesulfonamide to give E-2styrylquinolines.…”

A Facile Regioselectively Synthesis of 2‐Alkenylbenzo[1,2‐b:4,5‐b’]dithiophene by Pd/Cu/Ag‐Catalyzed C‐H Functionalization

“…In terms of atom‐economy and eco‐tolerance, Pd–assisted C−H functionalization of heteroarenes appears to be straightforward . After the first direct oxidative Heck reaction reported by Moritani and co‐workers, a number of Pd‐based catalytic systems have been developed to become a powerful tool for the direct alkenylation of arenes and heteroarenes . However, to the best of our knowledge, the site‐selective C‐2 Pd‐catalyzed alkenylation of BDT has not yet been explored.…”

“…[8][9][10][11] After the first direct oxidative Heck reaction reported by Moritani and co-workers, a number of Pd-based catalytic systems have been developed to become a powerful tool for the direct alkenylation of arenes and heteroarenes. [12][13][14][15][16][17][18][19][20][21] However, to the best of our knowledge, the site-selective C-2…”