1338935-90-2Relevant academic research and scientific papers
Synthesis of isochromene and related derivatives by rhodium-catalyzed oxidative coupling of benzyl and allyl alcohols with alkynes
Morimoto, Keisuke,Hirano, Koji,Satoh, Tetsuya,Miura, Masahiro
, p. 9548 - 9551 (2011)
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.
The oxidative annulation of tertiary benzyl alcohols with internal alkynes using an (electron-deficient η5-cyclopenta-dienyl)rhodium(III) catalyst under ambient conditions
Fukui, Miho,Hoshino, Yuki,Satoh, Tetsuya,Miura, Masahiro,Tanaka, Ken
, p. 1638 - 1644 (2014/06/09)
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.
Ruthenium(II)-catalyzed synthesis of isochromenes by C-H activation with weakly coordinating aliphatic hydroxyl groups
Nakanowatari, Sachiyo,Ackermann, Lutz
supporting information, p. 5409 - 5413 (2014/05/20)
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.
