scholarly journals Ni(ii)-catalyzed mono-selective ortho-arylation of unactivated aryl C–H bonds utilizing amino acids as a directing group

RSC Advances ◽  
2019 ◽  
Vol 9 (19) ◽  
pp. 10820-10824 ◽  
Author(s):  
Zhanqing Cong ◽  
Feng Gao ◽  
Hong Liu
Keyword(s):  
Amino Acids ◽  
Aryl Iodides ◽  
Directing Group

The nickel(ii)-catalyzed ortho-arylation of unactivated C–H bonds utilizing amino acids as directing groups with aryl iodides or bromides as coupling electrophiles is described.

Exogenous Directing Group Free, Ligand-Enabled gamma-C(sp3)–H Arylation of Free Primary Aliphatic Amines and α-Amino Esters

2019 ◽  
Author(s):  
Yongzheng Ding ◽  
Shuai Fan ◽  
Xiaoxi Chen ◽  
yuzhen gao ◽  
Gang Li
Keyword(s):  
Amino Acids ◽  
Large Scale ◽  
Free Ligand ◽  
Aliphatic Amines ◽  
Rapid Synthesis ◽  
Amino Esters ◽  
Directing Group ◽  
Large Scale Synthesis ◽  
Primary Aliphatic Amines

A Pdᴵᴵ-catalyzed, ligand-enabled gamma-C(sp3)–H arylation of free primary aliphatic amines and amino esters without using an exogenous directing group is reported. This reaction is compatible with unhindered free aliphatic amines, and it is also be applicable to the rapid synthesis of biologically and synthetically valuable unnatural α-amino acids. Large scale synthesis is also feasible using this method.<br>

Progress and perspectives on directing group-assisted palladium-catalysed C–H functionalisation of amino acids and peptides

2021 ◽  
Author(s):  
Sadegh Shabani ◽  
Yuezhou Wu ◽  
Hannah G. Ryan ◽  
Craig A. Hutton
Keyword(s):  
Amino Acids ◽  
Directing Group

A review of Pd-assisted, directing-group mediated C–H functionalisation of amino acids and peptides.

scholarly journals Synthesis of β-arylated alkylamides via Pd-catalyzed one-pot installation of a directing group and C(sp3)–H arylation

2016 ◽  
Vol 12 ◽  
pp. 1122-1126 ◽  
Author(s):  
Yunyun Liu ◽  
Yi Zhang ◽  
Xiaoji Cao ◽  
Jie-Ping Wan
Keyword(s):  
One Pot ◽  
Acyl Chlorides ◽  
Aryl Iodides ◽  
Directing Group

The synthesis of β-arylated alkylamides via alkyl C–H bond arylation has been realized by means of direct one-pot reactions of acyl chlorides, aryl iodides and 8-aminoquinoline. Depending on the structure of the starting materials, both single and double β-arylated alkylamides could be accessed.

scholarly journals Applications of tert-butanesulfinamide in the asymmetric synthesis of amines

2003 ◽  
Vol 75 (1) ◽  
pp. 39-46 ◽  
Author(s):  
J. A. Ellman
Keyword(s):  
Amino Acids ◽  
Asymmetric Synthesis ◽  
Nucleophilic Addition ◽  
Amino Alcohols ◽  
Wide Range ◽  
Aldehydes And Ketones ◽  
Directing Group ◽  
High Yields ◽  
Direct Condensation

tert-Butanesulfinamide is prepared using catalytic enantioselective methods in two steps from the extremely inexpensive oil waste by-product, tert-butyl disulfide. Direct condensation of tert-butanesulfinamide with aldehydes and ketones provides tert-butanesulfinyl imines in uniformly high yields. The tert-butanesulfinyl group activates the imines for the addition of many different classes of nucleophiles, serves as a powerful chiral directing group, and after nucleophilic addition is readily cleaved by treatment with acid. A wide range of highly enantioenriched amines, including α-branched and α,α-dibranched amines, α- and β-amino acids, 1,2 and 1,3-amino alcohols and α-trifluoromethyl amines are efficiently synthesized using this methodology.

Pd-Catalyzed directedCH-(hetero)arylation of cyclic α-amino acids: effects of substituents and the ring size

2019 ◽  
Vol 17 (17) ◽  
pp. 4342-4349 ◽  
Author(s):  
Valeriia Hutskalova ◽  
Pavel K. Mykhailiuk
Keyword(s):  
Amino Acids ◽  
Systematic Study ◽  
Ring Size ◽  
Directing Group ◽  
First Time ◽  
Cyclic Amino Acids

A systematic study on the directed Pd-catalyzed (hetero)arylation of 26 substituted cyclic α-amino acids at the C(3)-atom was performed. For the first time, the 7- and 8-membered cyclic amino acids were introduced to C–H activation. 8–Aminoquinoline was used as a directing group.

Expeditious synthesis of phenanthridines through a Pd/MnO2-mediated C–H arylation/oxidative annulation cascade from aldehydes, aryl iodides and amino acids

2020 ◽  
Vol 56 (18) ◽  
pp. 2775-2778 ◽  
Author(s):  
Jian Fan ◽  
Li Li ◽  
Jitan Zhang ◽  
Meihua Xie
Keyword(s):  
Amino Acids ◽  
Aryl Iodides

The expeditious access to phenanthridines through a Pd/MnO2-mediated arylation/oxidative annulation cascade from aldehydes, aryl iodides and amino acids is described.

Synthesis of Fluorenones from Benzaldehydes and Aryl Iodides: Dual C–H Functionalizations Using a Transient Directing Group

2017 ◽  
Vol 19 (5) ◽  
pp. 1140-1143 ◽  
Author(s):  
Xiao-Yang Chen ◽  
Seyma Ozturk ◽  
Erik J. Sorensen
Keyword(s):  
Aryl Iodides ◽  
Directing Group

Pd-Catalyzed Coupling of γ-C(sp3)–H Bonds of Oxalyl Amide-Protected Amino Acids with Heteroaryl and Aryl Iodides

2016 ◽  
Vol 81 (13) ◽  
pp. 5681-5689 ◽  
Author(s):  
Jian Han ◽  
Yongxiang Zheng ◽  
Chao Wang ◽  
Yan Zhu ◽  
Zhi-Bin Huang ◽  
...  
Keyword(s):  
Amino Acids ◽  
Aryl Iodides

scholarly journals Synthesis of amino acids and peptides with bulky side chains via ligand-enabled carboxylate-directed γ-C(sp3)–H arylation

2020 ◽  
Vol 11 (1) ◽  
pp. 290-294 ◽  
Author(s):  
Lei Liu ◽  
Yan-Hua Liu ◽  
Bing-Feng Shi
Keyword(s):  
Amino Acids ◽  
Side Chains ◽  
Directing Group

Pd-catalyzed ligand-enabled γ-C(sp3)–H arylation of tert-leucine and its derived peptides without using an external directing group via a less favored six-membered palladacycle is reported.

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