Synthesis of Unsymmetrical Biheteroarenes via Dehydrogenative and Decarboxylative Coupling: a Decade Update

New Strategy ◽

The Cross ◽

Acyl Donors ◽

Acid Esters

A new strategy for the synthesis of ketones is presented based upon the decarboxylative coupling of N-hydroxyphthalimide (NHP) esters with S-2-pyridyl thioesters. The reactions are selective for the cross-coupled product because NHP esters act as radical donors and the thioesters act as acyl donors. The reaction conditions are general and mild, with over 40 examples presented, including larger fragments and the 20-mer peptide Exendin(9-39) on solid support.

Connecting Remote C–H Bond Functionalization and Decarboxylative Coupling Using Simple Amines

10.26434/chemrxiv.9863363.v1 ◽

2019 ◽

Author(s):

Francisco de Azambuja ◽

Ming-Hsiu Yang ◽

Alexander Bruecker ◽

Paul Cheong ◽

Ryan Altman

Keyword(s):

Organic Molecules ◽

Mechanistic Studies ◽

Bond Functionalization ◽

Bond Forming ◽

The manuscript describes a Pd-catalyzed reaction of benzylic electrophiles that gives para-substituted arene products. Mechanistic studies suggest a mechanism involving a dearomative C–C bond-forming step, followed by base-mediated rearomatization. This mechanism is uncommon and underappreciated in Pd-catalysis and further exploitation of this mechanism should enable access to other organic molecules.

Ruthenium(ii)-catalyzed decarbonylative and decarboxylative coupling of isatoic anhydrides with salicylaldehydes: access to aryl 2-aminobenzoates

Organic & Biomolecular Chemistry ◽

10.1039/d1ob00027f ◽

2021 ◽

Vol 19 (12) ◽

pp. 2725-2730

Author(s):

Bidisha R. Bora ◽

Rashmi Prakash ◽

Sabera Sultana ◽

Sanjib Gogoi

Keyword(s):

Coupling Reactions ◽

Decarbonylative and decarboxylative coupling reactions of salicylaldehydes with isatoic anhydrides afford aryl 2-aminobenzoates.

Mn(OAc)3-Mediated Aerobic Oxidative Decarboxylative Coupling

Synfacts ◽

10.1055/s-0035-1560076 ◽

2015 ◽

Vol 11 (09) ◽

pp. 0972-0972

Keyword(s):

ChemInform Abstract: Palladium-Catalyzed Decarboxylative Coupling of Benzoic Acid Derivatives Using Hydrazone Ligands.

ChemInform ◽

10.1002/chin.201439095 ◽

2014 ◽

Vol 45 (39) ◽

pp. no-no

Author(s):

Takashi Mino ◽

Eri Yoshizawa ◽

Kohei Watanabe ◽

Taichi Abe ◽

Kiminori Hirai ◽

...

Keyword(s):

Benzoic Acid ◽

Benzoic Acid Derivatives ◽

Palladium Catalyzed ◽

Hydrazone Ligands

Phosphine-Free Palladium-Catalyzed Decarboxylative Coupling of Alkynylcarboxylic Acids with Aryl and Heteroaryl Halides

Advanced Synthesis & Catalysis ◽

10.1002/adsc.201200876 ◽

2013 ◽

Vol 355 (4) ◽

pp. 705-710 ◽

Cited By ~ 18

Author(s):

Police Vishnuvardhan Reddy ◽

Pottabathula Srinivas ◽

Manne Annapurna ◽

Suresh Bhargava ◽

Jorg Wagler ◽

...

Keyword(s):

Palladium Catalyzed

Copper-Catalyzed Decarboxylative Coupling of Alkynyl Carboxylates with 1,1-Dibromo-1-alkenes

The Journal of Organic Chemistry ◽

10.1021/jo400616r ◽

2013 ◽

Vol 78 (9) ◽

pp. 4551-4557 ◽

Cited By ~ 39

Author(s):

Zheng Huang ◽

Rui Shang ◽

Zi-Rong Zhang ◽

Xiao-Dan Tan ◽

Xiao Xiao ◽

...

Keyword(s):

ChemInform Abstract: Regioswitchable Palladium-Catalyzed Decarboxylative Coupling of 1,3-Dicarbonyl Compounds.

ChemInform ◽

10.1002/chin.201551052 ◽

2015 ◽

Vol 46 (51) ◽

pp. no-no

Author(s):

Miles Kenny ◽

Jeppe Christensen ◽

Simon J. Coles ◽

Vilius Franckevicius

Keyword(s):

Dicarbonyl Compounds ◽

Palladium Catalyzed

Decarboxylative dearomatization and mono-α-arylation of ketones

Chemical Communications ◽

10.1039/c6cc03672d ◽

2016 ◽

Vol 52 (49) ◽

pp. 7695-7698 ◽

Cited By ~ 9

Author(s):

Shehani N. Mendis ◽

Jon A. Tunge

Keyword(s):

Aromatic Ketones ◽

Ligand-controlled decarboxylative coupling of benzyl enol carbonates provides dearomatized products via enantiospecific coupling or alpha-aromatic ketones via dearomatization–rearomatization.