Reactions Involving Carbon–Carbon Bond Cleavage

Although they have historically played a relatively lesser role in organic synthesis, the appearance of a number of interesting methods that utilize C–C bond cleavage has prompted coverage in this chapter. Christopher W. Bielawski at the University of Texas at Austin found (Chem. Sci. 2012, 3, 2986) that the diamidocarbene 1 inserted into the C(O)–C(O) bond of dione 2 to produce 3 at room temperature. The use of oxalate monoester 5 for the decarboxylative cross-coupling with pyridine 4 to produce 6 was reported (Tetrahedron Lett. 2012, 53, 5796) by Yi-Si Feng at Hefei University of Technology. The team of Junichiro Yamaguchi and Kenichiro Itami at Nagoya University developed (J. Am. Chem. Soc. 2012, 134, 13573) a decarbonylative C–H coupling method that allowed for the merger of oxazoles 7 and 8 to form 9, an intermediate on the way to muscoride A. The decarboxylative alkenylation of alcohols, such as in the conversion of 10 and n-propanol to alcohol 11, was reported (Chem. Sci. 2012, 3, 2853) by Zhong-Quan Liu at Lanzhou University. Guangbin Dong at the University of Texas at Austin reported (J. Am. Chem. Soc. 2013, 134, 20005) a rhodium-catalyzed C–C bond activation strategy for the enantioselective conversion of benzocyclobutenone 12 to tricycle 13. Rhodium catalysis was also employed (J. Am. Chem. Soc. 2012, 134, 17502) by Masahiro Murakami at Kyoto University in the ring expansion of benzocyclobutenol 14 to form 15, the regioselectivity of which is opposite to that of the thermal reaction. The tandem semipinacol-type migration/aldol reaction of cyclohexenone 16 to produce 17 was developed (Org. Lett. 2012, 14, 5114) by Yong-Qiang Tu and Fu-Min Zhang at Lanzhou University. A procedure for the synthesis of complex cyclopentenone 19 by the addition of vinyl Grignard to cyclobutanedione 18 was reported (J. Org. Chem. 2012, 77, 6327) by Teresa Varea at the University of Valencia in Spain. Michael A. Kerr at the University of Western Ontario found (J. Org. Chem. 2012, 77, 6634) that treatment of cyclopropane hemimalonate 20 with azide led to the formation of 21, which can be readily reduced to the corresponding γ-aminobutyric ester.

Récupéré en direct depuis OpenAlex et désinversé. Les résumés ne sont pas conservés dans cette base de données : les index inversés représentent 8,6 Go des 9,3 Go de texte de la base, et le serveur dispose de 13 Go libres.