Organic Chemistry Portal
Organic Chemistry Highlights

Monday, May 26, 2014
Douglass F. Taber
University of Delaware

Organic Functional Group Interconversion

Alois Fürstner of the Max-Planck-Institut Mülheim devised (Angew. Chem. Int. Ed. 2013, 52, 14050. DOI: 10.1002/anie.201307584) a Ru catalyst for the trans-selective hydroboration of an alkyne 1 to 2. Qingbin Liu of Hebei Normal University and Chanjuan Xi of Tsinghua University coupled (Org. Lett. 2013, 15, 5174. DOI: 10.1021/ol402212g) the alkenyl zirconocene derived from 3 with an acyl azide to give the amide 4. Chulbom Lee of Seoul National University used (Angew. Chem. Int. Ed. 2013, 52, 10023. DOI: 10.1002/anie.201303669) a Rh catalyst to convert a terminal alkyne 5 to the ester 6. Laura L. Anderson of the University of Illinois, Chicago devised (Org. Lett. 2013, 15, 4830. DOI: 10.1021/ol402237w) a protocol for the conversion of a terminal alkyne 7 to the α-amino aldehyde 9.

Dewen Dong of the Changchun Institute of Applied Chemistry developed (J. Org. Chem. 2013, 78, 11956. DOI: 10.1021/jo401997v) conditions for the monohydrolysis of a bis nitrile 10 to the monoamide 11. Aiwen Lei of Wuhan University optimized (Chem. Commun. 2013, 49, 7923. DOI: 10.1039/C3CC43875A) a Ni catalyst for the conversion of the alkene 12 to the enamide 13. Kazushi Mashima of Osaka University optimized (Adv. Synth. Catal. 2013, 355, 3391. DOI: 10.1002/adsc.201300819) a boronic ester catalyst for the conversion of an amide 14 to the ester 15. Jean-François Paquin of the Université Laval prepared (Eur. J. Org. Chem. 2013, 4325. DOI: 10.1002/ejoc.201300289) the amide 17 by coupling an amine with the activated intermediate from reaction of an acid 16 with Xtal-Fluor E.

Steven Fletcher of the University of Maryland School of Pharmacy designed (Tetrahedron Lett. 2013, 54, 4624. DOI: 10.1016/j.tetlet.2013.06.049) the azodicarbonyl dimorpholide 18 as a reagent for the Mitsunobu coupling of 19 with 20. The reduced form of 18 was readily separated by extraction into water and reoxidized. Jens Deutsch of the Universität Rostock found (Chem. Eur. J. 2013, 19, 17702. DOI: 10.1002/chem.201302774) simple ligands for the Ru-mediated borrowed hydrogen conversion of an alcohol 22 to the amine 23. Ronald T. Raines of the University of Wisconsin devised (J. Am. Chem. Soc. 2013, 135, 14936. DOI: 10.1021/ja407822b) a phosphinoester for the efficient conversion in water of an azide 24 to the diazo 25. In the course of a synthesis of Birkenal, Shigefumi Kuwahara of Tohoku University effected (Eur. J. Org. Chem. 2013, 2780. DOI: 10.1002/ejoc.201300257) elimination of the lactone 26 to the alkene 27. At higher temperature the product 27 was isomerized to the endocyclic alkene.

Ning Jiao of Peking University effected (Angew. Chem. Int. Ed. 2013, 52, 7850. DOI: 10.1002/anie.201303376) cleavage of the aryl alkyne 28 to the amide 29. Wujiong Xia of the Harbin Institute of Technology used (Org. Lett. 2013, 15, 624. DOI: 10.1021/ol303437m) visible light to convert the aldehyde 30 to the ketone 31. Xihe Bi and Qun Liu of Northeast Normal University described (Angew. Chem. Int. Ed. 2013, 52, 11303. DOI: 10.1002/anie.201305010) the complementary degradation (not illustrated) of an aryl methyl ketone to the aromatic aldehyde.

D. F. Taber, Org. Chem. Highlights 2014, May 19.