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Synlett 2014; 25(6): 866-870
DOI: 10.1055/s-0033-1340841
DOI: 10.1055/s-0033-1340841
letter
An Efficient Protocol for the Carbon–Sulfur Cross-Coupling of Sulfenyl Chlorides with Arylboronic Acids using a Palladium Catalyst
Further Information
Publication History
Received: 11 December 2013
Accepted after revision: 27 January 2014
Publication Date:
06 March 2014 (online)
Abstract
An efficient protocol for carbon–sulfur bond formation is developed, which involves the cross-coupling of sulfenyl chlorides and arylboronic acids catalyzed by a novel palladium–Schiff base complex. Good to high product yields, short reaction times, and mild reaction conditions are important features of this new method.
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References and Notes
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- 16 Ligands HL1 and HL2 The ligands, 2-[2-(benzylthio)phenyliminomethyl]-4-bromophenol (HL1) and N-[2-(benzylthio)phenyl]salicyl-aldimine (HL2) were synthesized according to the literature method, see ref. 17. [PdL1Cl] (1a) 2-[2-(Benzylthio)phenyliminomethyl]-4-bromophenol (HL1) (199 mg, 0.50 mmol) was dissolved in EtOH (10 mL) and a solution of sodium tetrachloropalladate (153 mg, 0.52 mmol) in EtOH (10 mL) was added dropwise. The mixture was stirred in a water-bath at 90 °C for 0.5 h during which the color of the solution changed to bright orange–yellow. The solution was then allowed to stand for 2 h, which resulted in the formation of orange–red needle-like crystals suitable for X-ray diffraction. These were filtered, washed with 25% EtOH–H2O and dried under vacuum (10–2 Torr). The purity was assessed by TLC. Yield: 322 mg (86%); orange-red needles; mp 250 °C. IR (KBr): 1620 (s), 1439 (s), 752 (s), 560 (s) cm–1. Anal. Calcd for C20H15ONSPdBrCl: C, 44.55; H, 2.80; N, 2.60; S, 5.95. Found: C, 44.75; H, 2.90; N, 2.57; S, 5.85. [PdL2Cl] (1b) Complex 1b was prepared from N-[2-(benzylthio)phenyl]-salicylaldimine (HL2) using the same procedure as that described for 1a. Yield: 274 mg (80%); orange–red crystals; mp 256 °C. IR (KBr): 1600 (s), 1434 (s), 750 (s), 561 (s) cm–1. Anal. Calcd for C20H16ONSPdCl: C, 52.18; H, 3.47; N, 3.04; S, 6.97. Found: C, 52.23; H, 3.41; N, 3.16; S, 6.97. Sulfides 4; Typical Procedure A sealed tube was charged with sulfenyl chloride 2a (219 mg, 1 mmol), phenylboronic acid (3a) (135 mg, 1 mmol), K2CO3 (254 mg, 2 mmol), catalyst 1a (2 mol%, 10 mg) and DMF (2 mL). The mixture was stirred at 90 °C under an N2 atm for 5 h. After completion of the reaction, the mixture was cooled to r.t. and extracted with EtOAc (2 × 10 mL). The combined extracts were dried over anhydrous Na2SO4, filtered and the solvent removed under reduced pressure. The crude residue was purified by flash chromatography over silica gel to provide product 4a (166 mg, 89%).
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