187390-06-3

Upstream product

• 501-65-5 diphenyl acetylene 
• 7073-69-0 2-(2-bromophenyl)propanol 
• 98-01-1 furfural 
• 6975-99-1 6-dodecyne 
• 617-94-7 1-methyl-1-phenylethyl alcohol 
• 1942-45-6 4-Octyne 
• 69352-05-2 2-(2-iodophenyl)propan-2-ol 

Relevant academic research and scientific papers

Rhodium-catalyzed carbonylative annulation of 2-bromobenzylic alcohols with internal alkynes using furfural via β-aryl elimination

In spite of the significant progress made in transformations of unstrained benzylic (tert-)alcohols through β-aryl elimination, catalytic carbonylation has not yet been developed extensively because alkoxycarbonylation is probably favored over β-aryl elim

Palladium mediated domino reaction: Synthesis of isochromenes under aqueous medium

Isochromenes have been synthesized using palladium-catalyzed C-C and C-O bond forming reactions starting from ortho-bromo tertiary benzylic alcohols and internal acetylenes. Notably, this domino process is feasible by using the green solvent, water. The protocol exhibited a broad substrate scope and afforded various isochromenes.

Ruthenium(II)-catalyzed synthesis of isochromenes by C-H activation with weakly coordinating aliphatic hydroxyl groups

Cationic ruthenium(II) complexes have been employed for the highly effective oxidative annulation of alkynes with benzyl alcohols to deliver diversely decorated isochromenes. The hydroxyl-directed C-H/O-H functionalization process proceeded efficiently under an atmosphere of air. Detailed mechanistic studies were indicative of a kinetically relevant C-H metalation. Cationic ruthenium(II) complexes enabled highly efficient oxidative annulation of alkynes with benzylic alcohols to deliver isochromenes (see scheme). This aliphatic hydroxyl-directed C-H/O-H activation proceeded efficiently under an air atmosphere. Mechanistic studies were indicative of an irreversible C-H metalation as the rate-limiting step.

The oxidative annulation of tertiary benzyl alcohols with internal alkynes using an (electron-deficient η5-cyclopenta-dienyl)rhodium(III) catalyst under ambient conditions

It has been established that a dinuclear (electron-deficient η5-cyclopentadienyl)rhodium(III) complex catalyzes the oxidative annulation of tertiary benzyl alcohols with internal alkynes via sp2 C-H/O-H functionalization under ambient conditions (at room temperature under air) to give substituted isochromenes in good yields. The preference for annulation across electron-rich substrates over electron-deficient substrates was observed using this electron-deficient rhodium(III) complex.

Palladium-catalyzed annulation of internal alkynes in aqueous medium

To facilitate precatalyst recovery and reuse, we have developed a fluorous, oxime-based palladacycle 1 and demonstrated that it is a very efficient and versatile precatalyst for carbo- and heteroannulation of internal alkynes with functionalized aryl halides in aqueous medium. A uniform reaction condition for these annulation reactions was also developed.

Synthesis of isochromene and related derivatives by rhodium-catalyzed oxidative coupling of benzyl and allyl alcohols with alkynes

The straightforward synthesis of isochromene derivatives and related cyclic ethers is achieved by the rhodium-catalyzed oxidative coupling of α,α-disubstituted benzyl and allyl alcohols with alkynes. The hydroxy groups effectively act as the key function for the regioselective C-H bond cleavage.

Palladium catalyzed annulation of internal alkynes

A method is provided for the regioselective, palladium catalyzed carbo- or heteroannulation of internal alkynes by aryl iodides containing o-substituted side chains to yield aromatic carbocyclic and heterocyclic ring systems.