Pd(II)-Catalyzed Direct γ-C(sp3)-H Arylation between Free β2-Amino Esters and β3-Amino Esters and Aryl Iodides Using a Catalytic Transient Directing Group

2020 ◽  
Vol 85 (12) ◽  
pp. 7683-7693 ◽  
Author(s):  
Zhaohui Wang ◽  
Yangjie Fu ◽  
Qiyu Zhang ◽  
Hong Liu ◽  
Jiang Wang
Keyword(s):  
Amino Esters ◽  
Aryl Iodides ◽  
Directing Group

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>

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.

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

An insight into the synthesis of novel aryl-substituted alicyclic β-amino acid derivatives through substrate-directed palladium-catalysed regio- and stereoselective cross-coupling

RSC Advances ◽  
2015 ◽  
Vol 5 (18) ◽  
pp. 13628-13634 ◽  
Author(s):  
Melinda Nonn ◽  
Loránd Kiss ◽  
Mikko M. Hänninen ◽  
Ferenc Fülöp
Keyword(s):  
Amino Acid ◽  
Cross Coupling ◽  
Amino Acid Derivatives ◽  
Amino Esters ◽  
Aryl Iodides ◽  
Insight Into

Novel aryl-substituted alicyclic β-amino acid derivatives were synthesized through substrate-determined palladium-catalysed cross-coupling of aryl iodides with five- or six-membered cycloalkene β-amino esters.

scholarly journals Sulfonamide Directivity Enables Ni-Catalyzed 1,2-Diarylation of Diverse Alkenyl Amines

2020 ◽  
Author(s):  
Omar Apolinar ◽  
Van Tran ◽  
Michael A. Schmidt ◽  
Joseph Derosa ◽  
Keary Engle
Keyword(s):  
Electronic Properties ◽  
Coordination Mode ◽  
Dual Function ◽  
Nickel Catalysis ◽  
Sulfonyl Group ◽  
Aryl Iodides ◽  
Boronic Esters ◽  
Synthetic Utility ◽  
Directing Group ◽  
Amine Compounds

1,2-Diarylation of alkenyl sulfonamides with aryl iodides and aryl boronic esters under nickel catalysis is reported. The developed method tolerates coupling partners with disparate electronic properties and substitution patterns. 1,2- and 1,1-Disubstituted alkenes, as well as alkenes distal from the directing group, are all accommodated. Control experiments are consistent with a N–Ni coordination mode of the directing group, which stands in contrast to earlier reports on amide-directed 1,2-diarylation that involve carbonyl coordination. The synthetic utility of the method arises from the dual function of the sulfonamide as both a directing group and masked amine nucleophile. This is highlighted by various product diversifications where complex amine compounds are synthesized in a two-step sequence of <i>N</i>-functionalization and deprotection of the sulfonyl group.

scholarly journals Sulfonamide Directivity Enables Ni-Catalyzed 1,2-Diarylation of Diverse Alkenyl Amines

2020 ◽  
Author(s):  
Omar Apolinar ◽  
Van Tran ◽  
Michael A. Schmidt ◽  
Joseph Derosa ◽  
Keary Engle
Keyword(s):  
Electronic Properties ◽  
Coordination Mode ◽  
Dual Function ◽  
Nickel Catalysis ◽  
Sulfonyl Group ◽  
Aryl Iodides ◽  
Boronic Esters ◽  
Synthetic Utility ◽  
Directing Group ◽  
Amine Compounds

1,2-Diarylation of alkenyl sulfonamides with aryl iodides and aryl boronic esters under nickel catalysis is reported. The developed method tolerates coupling partners with disparate electronic properties and substitution patterns. 1,2- and 1,1-Disubstituted alkenes, as well as alkenes distal from the directing group, are all accommodated. Control experiments are consistent with a N–Ni coordination mode of the directing group, which stands in contrast to earlier reports on amide-directed 1,2-diarylation that involve carbonyl coordination. The synthetic utility of the method arises from the dual function of the sulfonamide as both a directing group and masked amine nucleophile. This is highlighted by various product diversifications where complex amine compounds are synthesized in a two-step sequence of <i>N</i>-functionalization and deprotection of the sulfonyl group.

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>

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.

Nickel-catalyzed regioselective arylation of aromatic amides with aryl iodides enabled by an N,O-bidentate directing group

2018 ◽  
Vol 16 (45) ◽  
pp. 8783-8790 ◽  
Author(s):  
Pinhua Li ◽  
Guan-Wu Wang ◽  
Hao Chen ◽  
Lei Wang
Keyword(s):  
Nickel Catalysis ◽  
Aryl Iodides ◽  
Directing Group

A bidentate directing group enabled ortho-arylation of C(sp2)–H bonds in aromatic carboxamides with aryl iodides under nickel-catalysis was developed.

Site-Selective γ-C(sp3)−H and γ-C(sp2)−H Arylation of Free Amino Esters Promoted by a Catalytic Transient Directing Group

2018 ◽  
Vol 24 (38) ◽  
pp. 9535-9541 ◽  
Author(s):  
Hua Lin ◽  
Chao Wang ◽  
Thomas D. Bannister ◽  
Theodore M. Kamenecka
Keyword(s):  
Free Amino ◽  
Amino Esters ◽  
Directing Group ◽  
Site Selective
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