Generation of benzyne from benzoic acid using C–H activation

Cant, Alastair A.; Roberts, Lee R.; Greaney, Michael F.

doi:10.1039/c0cc02547j

Cited by 78 publications

(31 citation statements)

References 46 publications

(5 reference statements)

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Subsequent valence isomerization affords ortho-quinone methides (96), which further react with second arynes to give various xanthenes in one pot (Scheme 82). 243 in situ-generated enolates (from malonates or b-diketones) or ketenimine anions (from arylacetonitriles), giving coumarins (98) and 2H-chromenes (99) in high yields (Scheme 84). 245,246 In contrast to the above [2 þ 2] cycloaddition, the reaction of sterically hindered thiones or selones with arynes produces stable four-membered cycloadducts, benzothietes (100), 94,247,248 and benzoselenetes (101) 249 (Scheme 85).…”

Section: [2 þ 2] Cycloadditionmentioning

confidence: 98%

4.09 Nucleophilic Coupling with Arynes

Yoshida

2014

Comprehensive Organic Synthesis II

View full text Add to dashboard Cite

Section: [2 þ 2] Cycloadditionmentioning

confidence: 98%

4.09 Nucleophilic Coupling with Arynes

Yoshida

2014

Comprehensive Organic Synthesis II

View full text Add to dashboard Cite

“…Catalytic aryne generation has emerged in recent years as an attractive strategy to access transition metal-associated arynes, with a few pioneering reports having demonstrated this principle. [36][37][38]40 As the metal can initiate both aryne formation and catalyse subsequent bond-forming transformations, the generation of metal-associated arynes is This journal is © The Royal Society of Chemistry 20xx…”

Section: Catalytic Aryne Generationmentioning

confidence: 99%

Recent advances in fluoride-free aryne generation from arene precursors

Idiris

Jones

2017

Org. Biomol. Chem.

View full text Add to dashboard Cite

Aryne chemistry has experienced a remarkable renaissance in recent years, with a significant increase in the synthetic applications reported for these highly valuable reactive intermediates. This resurgence of interest is in part due to the introduction of ortho-silylaryl triflates as precursors which can be activated under mild conditions using fluoride. Alternative fluoride-free strategies have received interest in the last decade, with a number of precursors to arynes and their activators reported. These approaches offer alternative modes of reactivity which prove, in some cases, to be orthogonal to those of ortho-silylaryl triflates. This review highlights some of the more recent fluoride-free methodologies developed to access aryne intermediates that start from arene-based precursors.

show abstract

“…In 2010, Greaney and co‐workers reported the use of benzoic acids to synthesize triphenylenes by trimerization of in situ‐generated benzynes under Pd(OAc) 2 catalysis . When alkynes were added to the reaction mixture, phenanthrenes and naphthalenes could also be accessed in stoichiometry‐governed product ratios.…”

Section: C−c Bond Formationmentioning

confidence: 99%

Carboxylic Acids as Directing Groups for C−H Bond Functionalization

Drapeau

Gooßen

2016

Chemistry A European J

268

View full text Add to dashboard Cite

The selective transformation of C-H bonds is one of the most desirable approaches to creating complexity from simple building blocks. Several directing groups are efficient in controlling the regioselectivity of catalytic C-H bond functionalizations. Among them, carboxylic acids are particularly advantageous, since they are widely available in great structural diversity and at low cost. The carboxylate directing groups can be tracelessly cleaved or may serve as the anchor point for further functionalization through decarboxylative couplings. This Minireview summarizes the substantial progress made in the last few years in the development of reactions in which carboxylate groups direct C-H bond functionalizations with formation of C-C, C-O, C-N, or C-halogen bonds at specific positions. It is divided into sections on C-C, C-O, C-N, and C-halogen bond formation, each of which is subdivided by reactions and product classes. Particular emphasis is placed on methods that enable multiple derivatizations by combining carboxylate-directed C-H functionalization with decarboxylative couplings.

show abstract

Generation of benzyne from benzoic acid using C–H activation

Abstract: ortho C-H activation of benzoic acids with Pd(II) generates an oxapalladacycle that can decarboxylate to produce a palladium-associated aryne. The arynes then undergo [2+2+2] trimerisation to afford triphenylenes.

Cited by 78 publications

References 46 publications

4.09 Nucleophilic Coupling with Arynes

4.09 Nucleophilic Coupling with Arynes

Recent advances in fluoride-free aryne generation from arene precursors

Carboxylic Acids as Directing Groups for C−H Bond Functionalization

Contact Info

Product

Resources

About