scholarly journals Palladium-catalyzed direct asymmetric C–H bond functionalization enabled by the directing group strategy

2020 ◽  
Vol 11 (47) ◽  
pp. 12616-12632 ◽  
Author(s):  
Ke Yang ◽  
Mengjie Song ◽  
Hao Liu ◽  
Haibo Ge
Keyword(s):  
Bond Functionalization ◽  
Group Strategy ◽  
Palladium Catalyzed ◽  
Directing Group

This minireview introduces Pd-catalyzed direct asymmetric C–H functionalization reactions using a directing group strategy.

scholarly journals Insights into Directing Group Ability in Palladium-Catalyzed C−H Bond Functionalization

2008 ◽  
Vol 130 (40) ◽  
pp. 13285-13293 ◽  
Author(s):  
Lopa V. Desai ◽  
Kara J. Stowers ◽  
Melanie S. Sanford
Keyword(s):  
Bond Functionalization ◽  
Palladium Catalyzed ◽  
Directing Group

Palladium-catalyzed phosphination and amination through C H bond functionalization on biphenyl: Amido-substituent as directing group

Tetrahedron ◽  
2019 ◽  
Vol 75 (3) ◽  
pp. 387-397 ◽  
Author(s):  
I-Hsiang Kao ◽  
Ching-Yu Wang ◽  
Yu-Chang Chang ◽  
Chu-Lun Wu ◽  
Yu-Jen Chiu ◽  
...  
Keyword(s):  
Bond Functionalization ◽  
Palladium Catalyzed ◽  
Directing Group

scholarly journals A Transient Directing Group Strategy Enables Enantioselective Multicomponent Organofluorine Synthesis

2021 ◽  
Author(s):  
Zhonglin Liu ◽  
Lucas Oxtoby ◽  
Mingyu Liu ◽  
Zi-Qi Li ◽  
Van Tran ◽  
...  
Keyword(s):  
Bioactive Compounds ◽  
Arylboronic Acids ◽  
Group Strategy ◽  
Palladium Catalyzed ◽  
Directing Group ◽  
Site Selective ◽  
Significant Attention ◽  
Three Component Coupling

The vicinal fluorofunctionalization of alkenes represents an expedient strategy for converting feedstock olefins into valuable fluorinated molecules and as such has garnered significant attention from the synthetic community; however, current methods remain limited in terms of scope and selectivity. Here we report the site-selective palladium-catalyzed three-component coupling of alkenylbenzaldehydes, arylboronic acids, and <i>N</i>-fluoro-2,4,6-trimethylpyridinium hexafluorophosphate facilitated by a transient directing group. The synthetically enabling methodology constructs vicinal stereocenters with excellent regio-, diastereo-, and enantioselectivities, forging products that map onto bioactive compounds.

Palladium-Catalyzed ortho-Monoacylation of Arenes with Aldehydes­ via 1,2,4-Benzotriazine-Directed C–H Bond Activation

Synthesis ◽  
2020 ◽  
Vol 52 (09) ◽  
pp. 1407-1416
Author(s):  
Bingcun Cui ◽  
Guosheng Huang ◽  
Jin Liu ◽  
Shaofen Jin ◽  
Yingxing Zhou ◽  
...  
Keyword(s):  
Functional Group ◽  
Bond Activation ◽  
Alternative Strategy ◽  
Bond Functionalization ◽  
Direct Modification ◽  
Palladium Catalyzed ◽  
Directing Group

An efficient palladium-catalyzed C–H bond functionalization/ortho-monoacylation reaction of 3-aryl-1,2,4-benzotriazines with (hetero)aryl or alkyl aldehydes has been developed, which offers a facile and alternative strategy for direct modification and further diversification of 3-aryl-1,2,4-benzotriazines. Bioactive 1,2,4-benzotriazine has been employed as a novel directing group for the palladium-catalyzed regioselective monoacylation of sp2 C–H bond protocol with broad substrate scope and good functional group tolerance.

scholarly journals A Transient Directing Group Strategy Enables Enantioselective Multicomponent Organofluorine Synthesis

2021 ◽  
Author(s):  
Zhonglin Liu ◽  
Lucas Oxtoby ◽  
Mingyu Liu ◽  
Zi-Qi Li ◽  
Van Tran ◽  
...  
Keyword(s):  
Bioactive Compounds ◽  
Arylboronic Acids ◽  
Group Strategy ◽  
Palladium Catalyzed ◽  
Directing Group ◽  
Site Selective ◽  
Significant Attention ◽  
Three Component Coupling

The vicinal fluorofunctionalization of alkenes represents an expedient strategy for converting feedstock olefins into valuable fluorinated molecules and as such has garnered significant attention from the synthetic community; however, current methods remain limited in terms of scope and selectivity. Here we report the site-selective palladium-catalyzed three-component coupling of alkenylbenzaldehydes, arylboronic acids, and <i>N</i>-fluoro-2,4,6-trimethylpyridinium hexafluorophosphate facilitated by a transient directing group. The synthetically enabling methodology constructs vicinal stereocenters with excellent regio-, diastereo-, and enantioselectivities, forging products that map onto bioactive compounds.

Stereospecific, Palladium-catalyzed C(sp3)–H Alkenylation and Alkynylation of a Proline Derivative Enabled by 8-Aminoquinoline as a Directing Group

2020 ◽  
Author(s):  
Aleksandra Balliu ◽  
Aaltje Roelofje Femmigje Strijker ◽  
Michael Oschmann ◽  
Monireh Pourghasemi Lati ◽  
Oscar Verho
Keyword(s):  
Carboxylic Acid ◽  
Building Blocks ◽  
Wide Range ◽  
Palladium Catalyzed ◽  
Directing Group ◽  
High Yields ◽  
Vinyl Iodides ◽  
Initial Results

<p>In this preprint, we present our initial results concerning a stereospecific Pd-catalyzed protocol for the C3 alkenylation and alkynylation of a proline derivative carrying the well utilized 8‑aminoquinoline directing group. Efficient C–H alkenylation was achieved with a wide range of vinyl iodides bearing different aliphatic, aromatic and heteroaromatic substituents, to furnish the corresponding C3 alkenylated products in good to high yields. In addition, we were able show that this protocol can also be used to install an alkynyl group into the pyrrolidine scaffold, when a TIPS-protected alkynyl bromide was used as the reaction partner. Furthermore, two different methods for the removal of the 8-aminoquinoline auxiliary are reported, which can enable access to both <i>cis</i>- and <i>trans</i>-configured carboxylic acid building blocks from the C–H alkenylation products.</p>

Theoretical and experimental studies of palladium-catalyzed site-selective C(sp3)−H bond functionalization enabled by transient ligands

2017 ◽  
Author(s):  
Haibo Ge ◽  
Lei Pan ◽  
Piaoping Tang ◽  
Ke Yang ◽  
Mian Wang ◽  
...  
Keyword(s):  
Bond Activation ◽  
Theoretical Calculations ◽  
Experimental Studies ◽  
Bond Functionalization ◽  
Aliphatic Ketones ◽  
Site Selectivity ◽  
Mechanistic Investigation ◽  
Palladium Catalyzed ◽  
Metal Catalyzed ◽  
Site Selective

Transition metal-catalyzed selective C–H bond functionalization enabled by transient ligands has become an extremely attractive topic due to its economical and greener characteristics. However, catalytic pathways of this reaction process on unactivated sp<sup>3</sup> carbons of reactants have not been well studied yet. Herein, detailed mechanistic investigation on Pd-catalyzed C(sp<sup>3</sup>)–H bond activation with amino acids as transient ligands has been systematically conducted. The theoretical calculations showed that higher angle distortion of C(sp2)-H bond over C(sp3)-H bond and stronger nucleophilicity of benzylic anion over its aromatic counterpart, leading to higher reactivity of corresponding C(sp<sup>3</sup>)–H bonds; the angle strain of the directing rings of key intermediates determines the site-selectivity of aliphatic ketone substrates; replacement of glycine with β-alanine as the transient ligand can decrease the angle tension of the directing rings. Synthetic experiments have confirmed that β-alanine is indeed a more efficient transient ligand for arylation of β-secondary carbons of linear aliphatic ketones than its glycine counterpart.<br><br>

scholarly journals Manganese-catalyzed selective C–H activation and deuteration by means of a catalytic transient directing group strategy

2021 ◽  
Author(s):  
Sara Kopf ◽  
Helfried Neumann ◽  
Matthias Beller
Keyword(s):  
Group Strategy ◽  
One Step ◽  
Directing Group

A shortcut to ortho-deuterated aldehydes: a catalytic directing group enables the manganese-catalyzed C–H activation and deuteration of benzaldehydes in one step.

Temporary (PO) directing group enabled carbazole ortho arylation via palladium catalysis

2021 ◽  
Vol 57 (16) ◽  
pp. 2021-2024
Author(s):  
Zhi-Chao Qi ◽  
Qin-Xin Lou ◽  
Yuan Niu ◽  
Shang-Dong Yang
Keyword(s):  
Palladium Catalysis ◽  
Palladium Catalyzed ◽  
Directing Group

An efficient palladium-catalyzed, temporary P(O) directing group assisted C–H bond arylation of carbazoles was achieved, accompanied by the directing group being self-shed spontaneously.

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