In(III)-TMSBr-Catalyzed Cascade Reaction of Diarylalkynes with Acrylates for the Synthesis of Aryldihydronaphthalene Derivatives

Abstract

A combined Lewis acid system comprising of two or more Lewis acids occasionally exhibits augmented catalytic activity in organic transformations which are otherwise unrealizable by either of the components exclusively. On the other hand, the efficient construction of multiple new C-C bonds and polycyclic structures in minimal steps remains a subject of great interest in both academia and industry. Herein we report an efficient method to assemble aryldihydronaphthalene derivatives via a cascade reaction of diarylalkynes with acrylates under the catalysis of a combined Lewis acid derived from In(III) salt and TMSBr.

Gold-Catalyzed Ascorbic Acid-Induced Arylative Carbocyclization of Alkynes with Aryldiazonium Tetrafluoroborates

“…Compound 3a bearing an n -butyl group gave 2 H -chromene 3c in a 58% yield. We were pleased by this result since the arylative carbocyclization methods described so far have not been applied to alkynes containing an alkyl group at the terminal position . Compounds 4a and 5a with a phenyl and a naphthyl group reacted with a 66% and 51% yield, respectively.…”

“…Complementary alkynes can be transformed into tetrasubstitued olefins by a less explored metal-catalyzed electrophilic carbofunctionalization (Figure ). It was initially described by Greany using a palladium catalyst and aryliodonium salt as an electrophile and was later extended by Gaunt, who used a copper source . Other metals like iron, calcium, indium, or borderline bismuth have been shown to be active in this transformation, and along with aryliodonium salts, alcohols, acetals, and acrylates have been used as an electrophilic source.…”

Sulfur-Mediated Electrophilic Cyclization of Aryl-Substituted Internal Alkynes

“…HRMS measurements were carried out on a TOF mass spectrometer. Substituted alkynes 1a , 1b , 1c , 1d , 1e , 1f , 1g , 1h , 1i , 1l , 1m , 1o , 1p , 1q , 1r , 1s , and 1t were known and prepared according to published procedures. Alkynes 1j , 1k , and 1n were unknown and were synthesized by Sonogashira coupling.…”

Experiment and Computational Study on Pd‐Catalyzed MIA‐Directed Ortho‐C−H Alkynlation of Phenylalanine

“…Phenylacetylene derivatives are highly valuable synthetic intermediates with a wide range of applications [1] . They can be used in the synthesis of various paracyclic systems, including five‐membered indane, [1a–c] indene, [1d–g] and six‐membered tetralin [1h–j] and naphthalene [1k–n] . Additionally, they are also utilized in the synthesis of aryl five and six‐membered structures such as cyclopentylbenzane, [1o–p] cyclopentylbenzene, [1q–r] phenylcyclohexane, [1s–t] and phenylcyclohexene.…”