Palladium/norbornene catalysis: a versatile aryl C–H hydroxyalkylation, alkyl cinnamate formation

Palladium/Norbornene Cooperative Catalysis

“…The choice of the protecting group in the indole substrate (47c) was also important, as use of the methyl protecting group only gave the direct Heck product. Free primary alcohol 63 and alkyl bromide 64 were tolerated under modified reaction conditions.…”

Metal–Organic Cooperative Catalysis in C–H and C–C Bond Activation

“…The reaction of 2-iodotoluene ( 258 ), in which one of the two ortho positions is blocked by a methyl group, with alkyl iodide 259 and acrylate 32 was also carried out using metal–organic cooperative catalysis by Pd(0)/norbornene to produce o- alkyl-, ipso -vinyl-toluene 260 (Table , entry 1). , …”

“…The reaction of 2-iodotoluene (258), in which one of the two ortho positions is blocked by a methyl group, with alkyl iodide 259 and acrylate 32 was also carried out using metal−organic cooperative catalysis by Pd(0)/norbornene to produce o-alkyl-, ipso-vinyl-toluene 260 (Table 1, entry 1). 132,133 In this reaction, alkyl iodide 259 and acrylate 32 are selectively coupled at the respective ipso and ortho positions of 258. The reaction pathway begins with oxidative addition of iodobenzene (258) with Pd(0) to afford aryl−Pd(II) iodide complex 277 (Scheme 45).…”

Alkylating Reagents Employed in Catellani‐Type Reactions

“…In 2009, the same group developed an efficient one‐pot synthesis of isoquinolin‐3‐one derivatives by utilizing N‐substituted 2‐haloacetamides as the alkylating reagents (Table , entry 4) . In 2012, the group of Jafarpour used the unprotected hydroxyl alkylbromide as the alkylating reagent; this provided a new strategy for the construction of biologically important ortho ‐hydroxyalkyl cinnamic acid derivatives (Table , entry 5) …”

“…[16] In 2012, the group of Jafarpour used the unprotectedh ydroxyl alkylbromide as the alkylating reagent;t his provided an ew strategy for the construction of biologically important ortho-hydroxyalkyl cinnamic acid derivatives( Ta ble 1, entry 5). [17] In 2013, the group of Lautens demonstrated the exploitation of 1,3-dibromopropane as the alkylating reagent in the Catellani reactiont op reparesubstituted aromatics that could be converted into aromatic aminoa cids in af ew steps (Table 1, entry 6). [18] In 2014, the group of Liu reported an ovel Catellanitype tandemp rocess that used commercially available trifluoroethyli odide as the alkylating reagent, affording the ortho-trifluoroethyl-substituted styrenes efficiently (Table 1, entry 7).…”