Protonation of 2H-Azaphosphirene Complexes: PN Bond Activation and Ring-Expansion Reactions

2009 ◽  
Vol 15 (11) ◽  
pp. 2602-2616 ◽  
Author(s):  
Holger Helten ◽  
Marianne Engeser ◽  
Dietrich Gudat ◽  
Reinhold Schilling ◽  
Gregor Schnakenburg ◽  
...  
Keyword(s):  
Bond Activation ◽  
Ring Expansion

Intramolecular CN Bond Activation and Ring-Expansion Reactions of N-Heterocyclic Carbenes

2014 ◽  
Vol 21 (4) ◽  
pp. 1434-1438 ◽  
Author(s):  
Patrick Hemberger ◽  
Andras Bodi ◽  
Johannes H. J. Berthel ◽  
Udo Radius
Keyword(s):  
Bond Activation ◽  
Ring Expansion ◽  
Heterocyclic Carbenes

Reactions Involving Carbon–Carbon Bond Cleavage

2015 ◽  
Author(s):  
Tristan H. Lambert
Keyword(s):  
Organic Synthesis ◽  
Bond Activation ◽  
Bond Cleavage ◽  
Ring Expansion ◽  
Thermal Reaction ◽  
Rhodium Catalysis ◽  
University Of Texas ◽  
Carbon Carbon Bond ◽  
University Of Technology ◽  
The University

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.

scholarly journals Silylene induced cooperative B–H bond activation and unprecedented aldehyde C–H bond splitting with amidinate ring expansion

2019 ◽  
Vol 55 (24) ◽  
pp. 3536-3539 ◽  
Author(s):  
V. S. V. S. N. Swamy ◽  
K. Vipin Raj ◽  
Kumar Vanka ◽  
Sakya S. Sen ◽  
Herbert W. Roesky
Keyword(s):  
Bond Activation ◽  
Ring Expansion ◽  
Ambient Conditions ◽  
Bond Splitting

Silylene mediated B–H and aldehyde C–H bond splitting were realized under ambient conditions.

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