Novel and efficient synthesis of sulfur-containing heterocycles using a hypervalent iodine(III) reagent

Abstract

A novel and efficient synthesis of sulfur-containing heterocycles from phenol ethers bearing an alkyl sulfide sidechain using a combined reagent of a hypervalent iodine(u1) species and BF3.Et20 is described.

Glycosylation Reaction of <i>Thioglycosides</i> by Using Hypervalent Iodine(III) Reagent as an Excellent Promoter

“…The spots and bands were detected by UV irradiation (254, 365 nm). was synthesized by the method in the literature, 31) i.e., BF 3 ·Et 2 O (268 mL, 2.12 mmol) was added to a solution of 2-deoxy-2-phthalimido-1,3,4,6-tetra-O-acetyl-D-glucopyranose (676 mg, 1.41 mmol), and p-octyloxybenzenethiol (506 mg, 2.12 mmol) in dichloromethane (5 mL) at 0°C and the mixture was stirred for 20 h at room temperature (r.t.). After the reaction, the reaction mixture was poured into ice water and extracted with ethyl acetate.…”

“…[18][19][20][21][22][23][24][25][26][27][28][29][30] We have been engaged in the development of the oxidation of the sulfur atom utilizing hypervalent iodine reagents to form an active iodonium intermediate. 31,32) Thus, we have recently developed novel methods of hypervalent iodine-induced glycosylation of thioglycoside. 33) Besides our study, a few methods have been reported as for the activation of thioglycosides with hypervalent iodines to date [34][35][36] ; however, activation of disarmed thioglycosides with hypervalent iodines still remains impractical and unavailable in the synthesis of biologically active oligosaccharides.…”

The Efficient Synthesis of Morphinandienone Alkaloids by Using a Combination of Hypervalent Iodine(III) Reagent and Heteropoly Acid

“…As for the chemical oxidation of 1 a with heavy metals, glaucine ( 3 a ) was usually obtained in moderate to good yields 10. Similar to heavy metal oxidation, the reaction of 1 a with PIFA/BF 3 ⋅Et 2 O in CH 2 Cl 2 gave 3 a in 58 % yield (entry 1) 12e. On the contrary, application of our prior conditions,13b the combination of PIFA and tungsto( IV ) phosphoric acid (H 3 [PW 12 O 40 ], ca.…”

Metal-Free Oxidative Cross-Coupling Reaction of Heteroaromatic and Related Compounds

“…As a result, we have developed the direct oxidative nucleophilic substitution of phenyl ethers with various nucleophiles using phenyliodine(III) bis(trifluoroacetate) (PIFA). [55][56][57] In further study, a combination of Lewis acid and PIFA was used to identify a biaryl coupling reaction of phenyl ether and alkyl arene via a cation radical intermediate. [58][59][60][61][62][63] The coupling reaction proceeds via cation radicals with the neutral molecule of the substrate to obtain a coupling product.…”