Construction of seven- and eight-membered carbocycles by Lewis acid catalyzed C(sp3)–H bond functionalization

2019 ◽  
Vol 55 (92) ◽  
pp. 13856-13859 ◽  
Author(s):  
Yuna Otawa ◽  
Keiji Mori
Keyword(s):  
Lewis Acid ◽  
Bond Functionalization ◽  
Acid Catalyzed

Concise construction of seven- or eight-membered carbocycles was accomplished by Lewis acid catalyzed C(sp3)–H bond functionalization.

Lewis Acid Catalyzed Benzylic C-H Bond Functionalization of Azaarenes; Addition to Imines and Enones

Synthesis ◽  
2012 ◽  
Vol 44 (14) ◽  
pp. 2185-2194 ◽  
Author(s):  
Shigeki Matsunaga ◽  
Motomu Kanai ◽  
Hirotomo Komai ◽  
Tatsuhiko Yoshino
Keyword(s):  
Lewis Acid ◽  
Bond Functionalization ◽  
Acid Catalyzed

ChemInform Abstract: Lewis Acid Catalyzed Benzylic C-H Bond Functionalization of Azaarenes: Addition to Enones.

ChemInform ◽  
2011 ◽  
Vol 42 (27) ◽  
pp. no-no
Author(s):  
Hirotomo Komai ◽  
Tatsuhiko Yoshino ◽  
Shigeki Matsunaga ◽  
Motomu Kanai
Keyword(s):  
Lewis Acid ◽  
Bond Functionalization ◽  
Acid Catalyzed

ChemInform Abstract: Lewis Acid Catalyzed Benzylic C-H Bond Functionalization of Azaarenes: Addition to Imines and Enones.

ChemInform ◽  
2012 ◽  
Vol 43 (45) ◽  
pp. no-no
Author(s):  
Hirotomo Komai ◽  
Tatsuhiko Yoshino ◽  
Shigeki Matsunaga ◽  
Motomu Kanai
Keyword(s):  
Lewis Acid ◽  
Bond Functionalization ◽  
Acid Catalyzed

Lewis Acid Catalyzed Benzylic C−H Bond Functionalization of Azaarenes: Addition to Enones

2011 ◽  
Vol 13 (7) ◽  
pp. 1706-1709 ◽  
Author(s):  
Hirotomo Komai ◽  
Tatsuhiko Yoshino ◽  
Shigeki Matsunaga ◽  
Motomu Kanai
Keyword(s):  
Lewis Acid ◽  
Bond Functionalization ◽  
Acid Catalyzed

Catalytic Carbonyl-Olefin Metathesis of Aliphatic Ketones: Iron(III) HomoDimers as Lewis Acidic Superelectrophiles

2018 ◽  
Author(s):  
Haley Albright ◽  
Paul S. Riehl ◽  
Christopher C. McAtee ◽  
Jolene P. Reid ◽  
Jacob R. Ludwig ◽  
...  
Keyword(s):  
Lewis Acid ◽  
Olefin Metathesis ◽  
Acid Activation ◽  
Lewis Acid Catalysts ◽  
Distinct Mode ◽  
Aliphatic Ketones ◽  
Carbon Carbon Bond ◽  
Metathesis Reactions ◽  
Acid Catalyzed

<div>Catalytic carbonyl-olefin metathesis reactions have recently been developed as a powerful tool for carbon-carbon bond</div><div>formation. However, currently available synthetic protocols rely exclusively on aryl ketone substrates while the corresponding aliphatic analogs remain elusive. We herein report the development of Lewis acid-catalyzed carbonyl-olefin ring-closing metathesis reactions for aliphatic ketones. Mechanistic investigations are consistent with a distinct mode of activation relying on the in situ formation of a homobimetallic singly-bridged iron(III)-dimer as the active catalytic species. These “superelectrophiles” function as more powerful Lewis acid catalysts that form upon association of individual iron(III)-monomers. While this mode of Lewis acid activation has previously been postulated to exist, it has not yet been applied in a catalytic setting. The insights presented are expected to enable further advancement in Lewis acid catalysis by building upon the activation principle of “superelectrophiles” and broaden the current scope of catalytic carbonyl-olefin metathesis reactions.</div>

Sign in / Sign up

Export Citation Format

Share Document