C-H vs. C-C

Chisato Mukai and co-workers from Kanazawa University have reported in JACS on a rhodium catalyzed transformation that either results in a C-C bond cleavage or C-H bond activation reaction depending on the ligand.

JACS paper

C-C bond breaking mechanism

Here’s an interesting paper where the authors used 18O2 to label one of the oxygens found in the product to investigate the mechanism. Now I’m going to be a little bit critical here but in the supporting information they put the 18O-label on the carbonyl oxygen but in the manuscript they don’t know if it is on the O-benzyl of the ester or the carbonyl oxygen. Moreover the abstract figure shows that the 18O is on the carbonyl oxygen but they really don’t know. It’s a bit deceiving in the paper because it kind of sounds like they determined it through GC-MS but in the supporting information I could not find the GC-MS trace. I guess there is a limitation in analytical technology to determine the position of the 18O. But still it is not clear from the paper that they don’t know which position the 18-oxygen is.

ACIE paper

Oxycyanation of olefins

Yoshiaki Nakao and co-workers from Kyoto University have reported in JACS on an intramolecular palladium catalyzed oxycyanation.

JACS paper

Alkyl chlorides from carboxylic acids

Chaozhong Li and co-workers from Shanghai Institute of Organic Chemistry have reported in JACS on a silver catalyzed decarboxylative chlorination.

JACS paper

C-C bond cleavage via SnCl4

Matthias Brewer and co-workers at the University of Vermont have reported in Organic Letters on a tin promoted C-C bond cleavage.

OL paper

Poof be gone

Alexander Butin and co-workers have reported in Tetrahedron Letters on the loss of a vinyl methyl ketone group from an indole.

TL paper

C-C bond coupling via C-C bond breaking

Zhang-Jie Shi and co-workers at Peking University have reported in JACS on a rhodium catalyzed C-C bond coupling reaction by cleaving the aryl-carbon bond in secondary aryl methanols.

JACS paper

Introducing a trifluoro group

Erick Carreira and co-worker have reported in ACIEE on a way to introduce a trifluoroethyl group onto either a cyclic ketone or aldehyde using a Zr-catalyst.

ACIEE paper

Breaking the C-C triple bond

Igor Alabugin and co-workers from Florida State have reported in JOC on a double Michael reaction that cleaves the C-C triple bond of an alkynone.

JOC paper

5,6-dihydroglaucogenin C synthesis

Weisheng Tian and co-workers at Shanghai Institute of Organic Chemistry have reported in ACIEE on their synthesis of a saturated glaucogenin C.

ACIEE paper