Merging Photoredox with Br?nsted Acid Catalysis: The Cross-Dehydrogenative C?O Coupling for sp3 C?H Bond Peroxidation
A photoredox and Br?nsted acid synergistically catalyzed cross-dehydrogenative C?O coupling reaction is developed in which isochroman peroxyacetals are formed through sp3 C?H bond peroxidation. The reported method is characterized by its extremely mild reaction conditions, excellent yields, and broad substrate scope. An oxocarbenium ion p-chlorobenzenesulfonate was speculated to be the reactive intermediate. The role of hemiacetals and oxygenated dimers on the effective stabilization of the oxocarbenium ion was investigated; the presence of acid appeared to establish equilibrium between hemiacetals and oxygenated dimers with the oxocarbenium ion pairs. The broad applicability of the method highlights the potential of the protocol for molecule synthesis.
Manganese dioxide-methanesulfonic acid promoted direct dehydrogenative alkylation of sp3 C-H bonds adjacent to a heteroatom
A manganese dioxide (MnO2)-methanesulfonic acid (CH 3SO3H) oxidation system has been developed to efficiently promote direct coupling of benzylic ethers and carbamates with simple ketones via oxidative C-H bond activation.
Synthesis of chromanyl and dihydrobenzofuranyl piperazines
The synthesis of a series of regioisomeric chromanyl and dihydrobenzofuranyl piperazines is described.
Favor, David A.,Johnson, Douglas S.,Powers, James J.,Li, Tingsheng,Madabattula, Rambabu
p. 3039 - 3041
(2008/02/06)
New substituted isochromans
Isochromans with substituents in the aromatic ring are described. They are synthesised by cyclisation of related chloromethyl-2-phenylethyl ethers. The activated 1-position of the isochromans is essential for obtaining potential drugs.
Unterhalt,Joestingmeier
p. 641 - 644
(2007/10/03)
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