Palladium(O)-catalyzed carbonylation of alkenyl- and aryl- borates and boronic acids with carbon monoxide

Biaryl Diketone Synthesis via Palladium‐catalyzed Carbonylative Coupling with Carbon Monoxide or Various Metal Carbonyls

“…Many studies have been dedicated to the synthesis of carbonylative coupling of aryl compounds such as the one pioneered by Heck . Carbonylative coupling has since been further developed to synthesize a range of carbon nucleophiles, including tin, copper, boron, zinc, aluminum, magnesium, and silicon . However, the synthesis of unsymmetrical biaryl ketones using electron‐deficient aryl electrophiles is limited owing to the direct coupling side reaction without carbonyl insertion.…”

Carbonylative Coupling of 4,4’-Diiodobiphenyl Catalyzed by Pd(NHC) Complex

“…This method is one of the most efficient and direct routes to synthesize aryl ketones as it forms tow carbon-carbon bonds in a single step, in contrast to the conventional method of introducing ketone functional group in a stepwise fashion. Carbonylative coupling has since been further developed to synthesize a range of carbon nucleophiles [12], including those of tin [13][14][15][16][17], copper [18][19][20][21][22], boron [23][24][25], zinc [26], aluminum [27], magnesium [28], and silicon [29][30][31]. Our purpose is to synthesize a new distyryl biphenyl arylene (DBA) derivative as a blue-emitting material.…”

Palladium‐Catalyzed Oxidative Carbonylative Coupling Reactions of Arylboronic Acids with Styrenes to Chalcones under Mild Aerobic Conditions

“…b Later on, Uemura and co‐workers showed the methoxycarbonylation of phenylboronic acid in methanol in the presence of [Pd(PPh 3 ) 4 ] and NaOAc as the catalytic system. They obtained methyl benzoate in 58 % yield together with benzophenone and biphenyl 7c. d More recently, Yamamoto reported the oxidative alkoxycarbonylation of arylboronates using a Pd(OAc) 2 /PPh 3 catalyst and a stoichiometric amount of benzoquinone as the oxidant 7f.…”

“…DPPM (2) 1 6 DPPE (2) 29 7 DPPP (2) 33 8 DPPB (2) 3 9 DPPPe (2) 0 10 DPPF (2) 0 11 DPEphos (2) 0 12 Xantphos (2) [a] PhB(OH) 2 (1 mmol), styrene (1 mmol), solvent (2 mL arylboronic acids as well as 2-naphthalenylboronic acid resulted in good to excellent yields of the corresponding chalcones (65-95 %; Table 3, entries 1-5). Fluoride-, chloride-, and even bromide-substituted phenylboronic acids gave 80-89 % of chalcones (Table 3, entries [6][7][8][9]. Similarly, the trifluoromethoxy-decorated phenylboronic acid was successfully coupled with styrene in 91 % yield ( Table 3, entry 10).…”