65490-19-9

Upstream product

• 1450-75-5 5-Bromo-2-hydroxyacetophenone 
• 1779-49-3 Methyltriphenylphosphonium bromide 

Downstream Products

• 73444-63-0 Acetic acid (E)-2-(5-bromo-2-hydroxy-phenyl)-propenyl ester 
• 73444-59-4 Acetic acid 4-bromo-2-(2-methyl-oxiranyl)-phenyl ester 
• 1246194-06-8 4-bromo-2-isopropenyl-1-(4-methoxyphenoxy)benzene 
• 1610359-54-0 8-bromo-4-methyl-1,2-diphenylspiro[4,5] deca-1,3,7,9-tetraen-6-one 
• 1610359-64-2 1,2-triphenylazulen-7-bromo-4(3aH)-one 
• 73444-56-1 Acetic acid 4-bromo-2-isopropenyl-phenyl ester 

Relevant academic research and scientific papers

OH-directed alkynylation of 2-vinylphenols with ethynyl benziodoxolones: A fast access to terminal 1,3-enynes

The first direct alkynylation of 2-vinylphenols was developed. The rationally optimized hypervalent iodine reagent TIPS-EBX in combination with [(CpRhCl2)2] as a C-H-activating transition metal catalyst enables the construction of a variety of highly substituted 1,3-enynes in high yields of up to 98 %. This novel C-H activation method shows excellent chemoselectivity and exclusive (Z)-stereoselectivity, and it is also remarkably mild and tolerates a variety of functional groups. Furthermore, synthetic modifications of the resulting 1,3-enynes were demonstrated. To our knowledge, this is the first example for an OH-directed C-H alkynylation with hypervalent iodine reagents.

Rhodium(III)-catalyzed dearomatizing (3 + 2) annulation of 2-alkenylphenols and alkynes

Appropriately substituted 2-alkenylphenols undergo a mild formal [3C+2C] cycloaddition with alkynes when treated with a Rh(III) catalyst and an oxidant. The reaction, which involves the cleavage of the terminal C-H bond of the alkenyl moiety and the dearomatization of the phenol ring, provides a versatile and efficient approach to highly appealing spirocyclic skeletons and occurs with high selectivity.

Synthesis of coumarins via Pd-catalyzed oxidative cyclocarbonylation of 2-vinylphenols

Palladium-catalyzed oxidative cyclocarbonylation of 2-vinylphenols constitutes a simple, direct method for the synthesis of coumarins. The reaction conditions, employing low pressures of CO, and air or 1,4- benzoquinone as the oxidant, are attractive in terms of environmental considerations and operational simplicity. Coumarins with a variety of functional groups were prepared in yields up to 85%.

Total synthesis of rodgersinol: A survey of the Cu(II)-mediated coupling of ortho-substituted phenols

Full details of studies directed toward the total synthesis of both enantiomers of rodgersinol are described. The key parts of our synthetic route to rodgersinol included the Cu(II)-mediated coupling of an arylboronic acid with an ortho-alkyl substituted