Efficient suzuki-miyaura coupling of deactivated aryl chlorides catalyzed by an oxime palladacycle

Synlett

Volumn , Issue 18, 2009, Pages 3011-3015

  Alonso, Diego A ^a   Civicos J F ^a   Nájera, Carmen ^a  

^a UNIVERSITY OF ALICANTE   (Spain)

Author keywords

Biaryls; Boronic acids; Cross coupling; Palladacycles; Suzuki reaction

Indexed keywords

4,4' DICHLOROBENZOPHENONE OXIME; BORONIC ACID DERIVATIVE; CHLORIDE; OXIME DERIVATIVE; PALLADACYCLE; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; POTASSIUM CARBONATE; SOLVENT; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CATALYST; CROSS COUPLING REACTION; IRRADIATION; MICROWAVE IRRADIATION; SUZUKI MIYAURA COUPLING REACTION; SUZUKI REACTION;

EID: 72049094304     PISSN: 09365214     EISSN: 14372096     Source Type: Journal    
DOI: 10.1055/s-0029-1218285     Document Type: Article

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36. Typical Procedure for the Suzuki Coupling under MW Irradiation Conditions (Table 2, Entry 3) A freshly stock soln of catalyst 1 (150 mg, 0.019 mmol) in DMF (2.5 mL) and [HP(t-Bu)3]BF4 (110 g, 0.0375 mmol) in DMF (2.5 mL) were previously prepared and used. A 10 mL MW vessel was charged with K2CO3 (1.5 mmol, 207 mg), TBAOH (0.15 mmol, 120 mg), PhB(OH)2 (1.88 mmol, 225 mg), catalyst 1 (250 mL of the stock soln, 0.0019 mmol, 15 mg, 0.5 mol% Pd), [HP(t-Bu)3]BF4 (250 mL of the stock soln, 0.00375 mmol, 11 mg), 4-chloroanisole (0.75 mmol, 92 mL), and DMF (1.5 mL). The vessel was sealed with a pressure lock, and the mixture was heated in air at 130 °C by a MW irradiation of 40 W for 20 min in a CEM Discover MW reactor. After allowing the reaction to cool down to r.t., the mixture was filtered through a pad of Celite and poured into an excess of H2O (5 mL) and extracted with Et2O (3 ×5 mL). The combined organic phases were washed with H2O (3 ×5 mL), dried (MgSO4), and evaporated. The obtained crude product was purified by recrystallization in MeOH-H2O (3:1), yielding 102 mg of pure 4-methoxybiphenyl (4a, 74%) as a white solid; mp 89-93 °C. 1H NMR (300 MHz, CDCl3): d = 7.57-7.51 (m, 4 H, ArH), 7.42 (t, J = 7.5 Hz, 2 H, ArH), 7.30 (t, J = 7.2 Hz, 1 H, ArH), 6.98 (d, J = 8.7 Hz, 2 H, ArH), 3.86 (s, 3 H, CHO). MS (EI, 70 eV): m/z (%) = 184 (100) [M+], 169 (49) [M+ - Me], 141 (49), 139 (13), 115 (35).