The Chromium‐Templated Carbene Benzannulation Approach to Densely Functionalized Arenes (Doetz Reaction)

Abstract

Organic chemistryOrganic chemistry Z 0200The Chromium-Templated Carbene Benzannulation Approach to Densely Functionalized Arenes (Doetz Reaction) -[225 refs.]. -(DOETZ, K. H.; STENDEL, J. J.; Modern Arene Chem. 2002, 250-296; Kekule-Inst. Org. Chem. Biochem., Rhein. Friedrich-Wilhelms-Univ., D-53121 Bonn, Germany; Eng.) -Lindner 30-271

Liquid Dynamics Determine Transition Metal‐N‐Heterocyclic Carbene Complex Formation

“…N ‐Heterocyclic carbenes (NHCs) are widely used as ligands in transition metal catalysis, enabling efficient routes for organic synthesis [1–4] . The preparation of these complexes from the metal compound and the azolium cation has been based on four main methods.…”

“…N-Heterocyclic carbenes (NHCs) are widely used as ligands in transition metal catalysis, enabling efficient routes for organic synthesis. [1][2][3][4] The preparation of these complexes from the metal compound and the azolium cation has been based on four main methods. In the "free carbene route" (Figure 1A), the azolium cation is first deprotonated by a strong base to form a free NHC, followed by the reaction of this species with the metal to form the desired complex.…”

Efficient carbene transfer reactivity mediated by Fe(ii) complexes supported by bulky alkoxides

“…There is long-standing interest in the chemistry of metallocarbenes, one of the most important functionalities in organometallic chemistry. [1][2][3][4][5][6][7][8][9][10][11][12][13][14][15] The reactivity of a metallocarbene is determined by its electronic structure. 2,15 Common types of metallocarbenes include nucleophilic Schrock carbenes, 2,3 electrophilic Fischer carbenes, 2,4 and carbene radicals.…”

“…[1][2][3][4][5][6][7][8][9][10][11][12][13][14][15] The reactivity of a metallocarbene is determined by its electronic structure. 2,15 Common types of metallocarbenes include nucleophilic Schrock carbenes, 2,3 electrophilic Fischer carbenes, 2,4 and carbene radicals. [6][7][8]15 The reactivity difference between different types of metallocarbenes is most convincingly illustrated via their reactions with olefins.…”

“…Whereas nucleophilic carbenes usually demonstrate olefin metathesis, 2 both electrophilic and radical carbenes catalyze cyclopropanation. 4,7,13–15 However, while electrophilic carbenes usually demonstrate two-electron concerted reactivity with olefins, radical carbenes typically exhibit one-electron stepwise reactivity. 15 In addition to their reactions with olefins, metallocarbenes have been previously shown to react with isocyanides to form ketenimines, although this reactivity is generally stoichiometric.…”