Methanol from CO2 and H2

Melanie Sanford and colleague have come up with a recipe to convert carbon dioxide and hydrogen gas to methanol using three different catalysts.  The set up is interesting of course because it’s not your typical round bottom flask reaction – they used a pressure vessel containing the catalysts and added CO2 and H2.

JACS paper

That’s not normal reactivity

Xiaoming Feng and co-workers at Sichuan University have reported in JACS on an alpha-nitrogenation reaction of a ketone using an alpha-diazoester as the electrophile.  Normally we see alpha-diazoesters react as carbene precursors by losing N2 gas but I didn’t know that the nitrogen can also be an electrophile…

JACS paper

Sc-catalyzed C-C bond insertion

Jason Kingsbury and co-workers from Boston College have reported in Organic Letters on a scandium catalyzed insertion of a carbon unit into the alpha-position of a cyclic ketone.

 

OL paper

Hydride Shift and Hydride Shift

Takahiko Akiyama and co-workers at Gakushuin University have reported in JACS on a carbon-carbon bond cleaving process followed by a carbon-carbon bond forming process using a scandium (III) triflate catalyst.

JACS paper

Gold vs. Scandium

This paper by Junliang Zhang and co-worker from East China Normal University illustrates the difference between using a gold catalyst and a scandium catalyst.  Usually you might predict in a transition metal catalyzed reaction that the metal is just a large cation so the metal doesn’t make a difference.  However, this is not always the case and here we see how gold’s alkynophilicity yields the furan product – it’s a matter of whether the metal likes oxygen vs. carbon (excuse the anthropomorphism).

Chem Comm paper

Four to Five Ring Expansion

Jason Kingsbury and co-workers from Boston College have published in Organic Letters on the use of TMS-diazomethane to expand a cyclobutanone to a cyclopentanone.

OL paper

Carbonyl Ene Reaction

Teck-Peng Loh and co-workers at Nanyang Technological University in Singapore have published in JACS on a carbonyl ene reaction mediated by scandium.

JACS paper

Scandium Catalyzed Roskamp Reaction

Xiaoming Feng and co-workers at Sichuan University have published in JACS on a scandium triflate catalyzed Roskamp reaction.

JACS paper

Fawcettimine Synthesis

Michael Jung and co-worker at UCLA have published in Organic Letters on a total synthesis of fawcettimine via a scandium triflate mediated cyclopropane opening to form the cyclopentane ring in the alkaloid.

OL paper