Palladium-Catalyzed Amidation and Amination of (Hetero)aryl Chlorides under Homogeneous Conditions Enabled by a Soluble DBU/NaTFA Dual-Base System DOI
Gregory L. Beutner, John R. Coombs, Rebecca A. Green

et al.

Organic Process Research & Development, Journal Year: 2019, Volume and Issue: 23(8), P. 1529 - 1537

Published: June 17, 2019

The palladium-catalyzed coupling of aryl and heteroaryl chlorides with primary amides under mild homogeneous reaction conditions is reported. Successful C–N enabled by the use a unique "dual-base" system consisting DBU NaTFA, which serve as proton acceptor halide scavenger, respectively, using low catalyst loadings (0.5 mol %) readily available, air-stable palladium precatalysts. DBU/NaTFA also enables room-temperature amines tolerant variety base-sensitive functional groups.

Language: Английский

Synthesis of Functionalized Alkenes by a Transition-Metal-Free Zweifel Coupling DOI
Roly J. Armstrong, Worawat Niwetmarin, Varinder K. Aggarwal

et al.

Organic Letters, Journal Year: 2017, Volume and Issue: 19(10), P. 2762 - 2765

Published: April 28, 2017

The Zweifel reaction is a powerful method for the synthesis of alkenes, serving as transition-metal-free alternative to Suzuki–Miyaura reaction. To date, scope coupling has been rather narrow and focused mainly on vinyllithium reagents synthesize simple aryl- alkyl-substituted olefins. Herein, development general process enabling Grignard or organolithiums described. This enables enantiospecific wide variety functionalized acyclic cyclic olefin products.

Language: Английский

Citations

84

Nickel‐Catalyzed Enantioselective Conjunctive Cross‐Coupling of 9‐BBN Borates DOI
Matteo Chierchia, Chunyin M. Law, James P. Morken

et al.

Angewandte Chemie International Edition, Journal Year: 2017, Volume and Issue: 56(39), P. 11870 - 11874

Published: July 25, 2017

Catalytic enantioselective conjunctive cross-coupling between 9-BBN borate complexes and aryl electrophiles can be accomplished with Ni salts in the presence of a chiral diamine ligand. The reactions furnish derivatives an fashion these are converted to alcohols amines, or engaged other stereospecific C-C bond forming reactions.

Language: Английский

Citations

84

Diastereoselective and Enantioselective Conjunctive Cross-Coupling Enabled by Boron Ligand Design DOI

Jesse A. Myhill,

Christopher A. Wilhelmsen, Liang Zhang

et al.

Journal of the American Chemical Society, Journal Year: 2018, Volume and Issue: 140(45), P. 15181 - 15185

Published: Oct. 30, 2018

Enantio- and diastereoselective conjunctive cross-coupling of β-substituted alkenylboron "ate" complexes is studied. Whereas β-substitution shifts the chemoselectivity catalytic reaction in favor Suzuki–Miyaura product, use a boronic ester ligand derived from acenaphthoquinone allows process to even with substituted substrates.

Language: Английский

Citations

81

Stereospecific Allylic Functionalization: The Reactions of Allylboronate Complexes with Electrophiles DOI Creative Commons
Cristina García‐Ruiz, Jack L.‐Y. Chen, Christopher Sandford

et al.

Journal of the American Chemical Society, Journal Year: 2017, Volume and Issue: 139(43), P. 15324 - 15327

Published: Oct. 13, 2017

Allylboronic esters react readily with carbonyls and imines (π-electrophiles), but are unreactive toward a range of other electrophiles. By addition an aryllithium, the corresponding allylboronate complexes display enhanced nucleophilicity, enabling to electrophiles (tropylium, benzodithiolylium, activated pyridines, Eschenmoser's salt, Togni's reagent, Selectfluor, diisopropyl azodicarboxylate (DIAD), MeSX) in high regio- stereocontrol. This protocol provides access key new functionalities, including quaternary stereogenic centers bearing moieties such as fluorine trifluoromethyl group. The were determined be 7 10 orders magnitude more reactive than parent boronic ester.

Language: Английский

Citations

69

Palladium-Catalyzed Amidation and Amination of (Hetero)aryl Chlorides under Homogeneous Conditions Enabled by a Soluble DBU/NaTFA Dual-Base System DOI
Gregory L. Beutner, John R. Coombs, Rebecca A. Green

et al.

Organic Process Research & Development, Journal Year: 2019, Volume and Issue: 23(8), P. 1529 - 1537

Published: June 17, 2019

The palladium-catalyzed coupling of aryl and heteroaryl chlorides with primary amides under mild homogeneous reaction conditions is reported. Successful C–N enabled by the use a unique "dual-base" system consisting DBU NaTFA, which serve as proton acceptor halide scavenger, respectively, using low catalyst loadings (0.5 mol %) readily available, air-stable palladium precatalysts. DBU/NaTFA also enables room-temperature amines tolerant variety base-sensitive functional groups.

Language: Английский

Citations

65