Recent Advances of the Access to Indolinones via C—H Bond Functionalization/Cyclization Cascade Strategy

Recent Advances in Radical-Initiated C(sp3)–H Bond Oxidative Functionalization of Alkyl Nitriles

“…Considerable research interest has been attracted into the areas of tandem radical addition–cyclization reactions for the concise construction of molecular complexity and biological frameworks in organic synthesis . Normally, free-radical-initiated cyclization of activated alkenes 55 with different precursors proceeds via a sequence of radical addition and intramolecular homolytic aromatic substitution (HAS) (Scheme ).…”

Desulfonylation via Radical Process: Recent Developments in Organic Synthesis

“…To date, easily accessible N -aryl amides bearing a suitable pendant olefin have been considered as an exceptional precursor to N-heterocycles through the addition of carbon- or heteroatom-centered radicals and subsequent alkene difunctionalization. − Recognizing the need in this area, a Brønsted-base-assisted and photoredox-catalyzed intramolecular 5- exo -trig cyclization/intermolecular radical addition/elimination was developed to assemble alkyne- and alkene-decorated γ-lactams (pyrrolidin-2-ones), cyclic carbamates, and urea derivatives (Scheme A) . As such, the formation of two new C–C/C–N bonds and a new five-membered heterocyclic ring was accomplished in this synthetic strategy aiming at scaffold diversity (Scheme B).…”

“…Difunctionalization of unsaturated alkenes is considered to be attractive, as it allows the introduction of two versatile handles in a one-step manipulation. − As a logical extension of the radical addition cascade, the group of Hu further disclosed a simple fluoroalkylation–hydroxylation of alkenes with fluorinated sulfone and H 2 O (Scheme A) . By using various fluorinated sulfones and styrenes, β-fluoroalkyl benzyl alcohols were synthesized through the regioselective formation of C­(sp 3 )–CF 2 X and C­(sp 3 )–O bonds regardless of terminal or internal alkenes (Scheme B).…”

Syntheses of 3,3-Disubstituted Dihydrobenzofurans, Indolines, Indolinones and Isochromanes by Palladium-Catalyzed Tandem Reaction Using Pd(PPh3)2Cl2/(±)-BINAP as a Catalytic System

“…Compound V exhibits selective 5-hydroxytryptamine7 (5-HT 7 ) antagonist activity (K i = 0.79 nm) [13] and alstonisine (VI) also reveals antiplasmodial activity against Plasmodium falciparum, with an IC50 (half maximal inhibitory concentration) of 7.6 µM [14] (Figure 1). Therefore, organic chemists around the world made extensive efforts to develop the highly efficient methods of constructing these heterocycles [15][16][17][18][19][20][21][22][23][24][25][26][27][28]. Of these molecules, 3,3-disubsitituted five-membered chemists around the world made extensive efforts to develop the highly efficient methods of constructing these heterocycles [15][16][17][18][19][20][21][22][23][24][25][26][27][28].…”

“…The domino reactions of the synthesis of them were summarized mainly as follows: (i) the Pd or Ni-catalyzed cyclocarbopalladation/coupling fractions, in which the process was initiated by Heck cyclization of a starter (halide) and a relay (alkene), followed by intermolecular coupling reactions with a terminator (organometallic reagents, alkenes, alkynes, etc. ), including Suzuki, Stille, Heck, Sonogashira, C-H activation, carbonylation and amination and so forth [15][16][17]22,24,25,[29][30][31][32][33][34][35][36][37][38][39][40][41][42][43][44]; (ii) the C-H oxidative radical coupling reactions, in which these transformations were based on tandem radical addition/cyclization in the presence of oxidants with/without metal catalysts [18][19][20][21]23,26,[45][46][47][48][49][50][51][52][53][54][55]; and (iii) the other reactions [24,[56][57][58][5...…”