SCOPUS 정보 검색 플랫폼

Synlett

Volumn , Issue 2, 2008, Pages 255-259

Polyionic heterogeneous phenylating agent for base-free Suzuki-Miyaura coupling reaction

(4) Basu, Basudeb a Das, Sajal a Kundu, Sekhar a Mandal, Bablee a

a UNIVERSITY OF NORTH BENGAL (India)

Author keywords

Base free conditions; Biphenyls; Polyionic resins; Suzuki Miyaura coupling; Tetraphenylborate

Indexed keywords

HALIDE; PALLADIUM; POLACRILIN; RESIN; TETRAPHENYLBORON;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; SUZUKI REACTION; SYNTHESIS;

EID: 38849095192 PISSN: 09365214 EISSN: None Source Type: Journal
DOI: 10.1055/s-2008-1000874 Document Type: Article

Times cited : (9)

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- Representative Procedure for Suzuki-Miyaura Reaction: A mixture of 3-iodotoluene (218 mg, 1 mmol, Amberlite resin (Ph4B- form, 1 g, 1.14 mmol) and Pd(OAc)2 (4.5 mg, 2 mol, was taken in DMF (2 mL) and heated in an oil bath at 85°C for 2 h. After cooling, the reaction mixture was diluted with H2O (5 mL) and the resin was filtered off. The filtrate was extracted with Et2O (3 x 15 mL) and the combined organic layers were dried over anhyd Na2SO4. Removal of the solvent left an oily residue, which was passed through a short column of silica gel (60-120 mesh) eluting with light petroleum to afford 3-phenyltoluene as a colorless liquid (161 mg, yield 96, IR (neat, 3031, 2900, 1604 cm-1. 1H NMR (300 MHz, CDCl3, δ, 7.84-7.87 (m, 2 H, 7.56-7.71 (m, 6 H, 7.42 (d, J, 7.2 Hz, 1 H, 2.67 (s, 3 H, 13C NMR 75 MHz, CDCl3, δ, 141
- 3): δ = 141.3, 141.2, 138.2, 128.7, 128.6, 127.94, 127.89, 127.2, 127.1, 124.2, 21.5.

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- 4 solution. The resulting borate-bound resin could be reused for the SM reaction. Employing the recovered and recharged resin (tetraphenylborate form) for SM coupling with 3-iodotoluene (1 mmol scale), provided the desired biaryl in 95% yield. The three subsequent runs gave the biaryl in 92%, 92% and 88% yields.
- 4 solution. The resulting borate-bound resin could be reused for the SM reaction. Employing the recovered and recharged resin (tetraphenylborate form) for SM coupling with 3-iodotoluene (1 mmol scale), provided the desired biaryl in 95% yield. The three subsequent runs gave the biaryl in 92%, 92% and 88% yields.

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