1619992-33-4

Upstream product

• 1130782-28-3 1,1-dibromo-6-phenylspiro[2.5]octane 
• 87143-17-7 4-phenyl-1-methylenecyclohexane 
• 4894-75-1 1-phenyl-4-cyclohexanone 

Downstream Products

• 1619992-44-7 (E)-4-(4-(1,2,3,6-tetrahydro-[1,1'-biphenyl]-4-yl)vinyl)-1,1'-biphenyl 

Relevant academic research and scientific papers

Rhodium-Catalyzed Intermolecular Cyclopropanation of Benzofurans, Indoles, and Alkenes via Cyclopropene Ring Opening

The generation of metal carbenoids via ring opening of cyclopropenes by transition metals offers a simple entry into highly reactive intermediates. Herein, we describe a diastereoselective intermolecular rhodium-catalyzed cyclopropanation of heterocycles and alkenes using cyclopropenes as carbene precursors with a low loading of a commercially available rhodium catalyst. The reported method is scalable and could be performed with catalyst loadings as low as 0.2 mol %, with no impact to the reaction yield or selectivity.

Stereoselective Synthesis of Vinylcyclopropa[ b]indolines via a Rh-Migration Strategy

A mild rhodium catalytic system has been developed to synthesize vinylcyclopropa[b]indolines through cyclopropanation of indoles with vinyl carbenoids generated from ring opening of cyclopropenes in situ. By employing a Rh-migration strategy, the products can be obtained with good to excellent E:Z ratios (≤99:1) and complete diastereoselectivity (≤99:1). This method is easy, has a low catalyst loading, and works for a broad range of functionalities.

Synthesis of Functionalized α-Vinyl Aldehydes from Enaminones

An efficient RhII-catalyzed synthesis of functionalized α-vinyl aldehydes with high E/Z stereoselectivity was developed. The reaction mediates the cyclopropanation of enaminones with vinyl carbenoids that are generated from cyclopropenes in situ to give the aminocyclopropane intermediates. Selective C?C bond cleavage of the cyclopropane intermediates leads to formation of α-vinyl aldehyde derivatives with high E/Z selectivity. This method proceeds at room temperature under very mild reaction conditions and works with a broad substrate scope.

Rh(II)-Catalyzed [2,3]-Sigmatropic Rearrangement of Sulfur Ylides Derived from Cyclopropenes and Sulfides

(Chemical Equation Presented) A new type of Rh2(OAc)4-catalyzed [2,3]-sigmatropic rearrangement of sulfur ylides is reported. A series of cyclopropenes were successfully employed for [2,3]-sigmatropic rearrangement by a reaction with either allylic or propargylic sulfides. Under the optimized conditions, the reaction afforded the products in moderate to excellent yields. In these transformations, the vinyl metal carbenes generated in situ from the cyclopropenes were effectively trapped by sulfides, resulting in the formation of corresponding products upon [2,3]-sigmatropic rearrangements.