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.

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.

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

scholarly journals Nickel-Catalyzed Ipso-Borylation of Silyloxyarenes via C–O Bond Activation

2021 ◽  
Author(s):  
Wesley Pein ◽  
Eric Wiensch ◽  
John Montgomery
Keyword(s):  
Bond Activation ◽  
Cross Coupling ◽  
Coupling Reactions ◽  
Nickel Catalysis ◽  
Silyl Ethers ◽  
Cross Coupling Reactions ◽  
Boronic Esters ◽  
Directing Group ◽  
Aromatic Systems ◽  
Oxygen Bond

A mild method to convert silyloxyarenes to pinacol boronic esters using nickel catalysis is described. In contrast to other borylation protocols of relatively inert C–O bonds, the method is competent in activating the carbon-oxygen bond of silyloxyarenes in isolated aromatic systems lacking a directing group. The catalytic functionalization of benzyl silyl ethers was also achieved under these conditions. Orthogonal reactivity of silyloxyarenes vs other electrophiles was demonstrated in the case of several cross-coupling reactions wherein the unaffected silyloxarene could be functionalized subsequently.

scholarly journals Nickel-Catalyzed Ipso-Borylation of Silyloxyarenes via C–O Bond Activation

2021 ◽  
Author(s):  
Wesley Pein ◽  
Eric Wiensch ◽  
John Montgomery
Keyword(s):  
Bond Activation ◽  
Cross Coupling ◽  
Coupling Reactions ◽  
Nickel Catalysis ◽  
Silyl Ethers ◽  
Cross Coupling Reactions ◽  
Boronic Esters ◽  
Directing Group ◽  
Aromatic Systems ◽  
Oxygen Bond

A mild method to convert silyloxyarenes to pinacol boronic esters using nickel catalysis is described. In contrast to other borylation protocols of relatively inert C–O bonds, the method is competent in activating the carbon-oxygen bond of silyloxyarenes in isolated aromatic systems lacking a directing group. The catalytic functionalization of benzyl silyl ethers was also achieved under these conditions. Orthogonal reactivity of silyloxyarenes vs other electrophiles was demonstrated in the case of several cross-coupling reactions wherein the unaffected silyloxarene could be functionalized subsequently.

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.

Synthesis of S-aryl thioesters via palladium-catalyzed thiocarbonylation of aryl iodides and aryl sulfonyl hydrazides

2020 ◽  
Vol 7 (19) ◽  
pp. 2938-2943
Author(s):  
Yeojin Kim ◽  
Kwang Ho Song ◽  
Sunwoo Lee
Keyword(s):  
Aryl Iodide ◽  
Aryl Iodides ◽  
Palladium Catalyzed

Aryl sulfonyl hydrazide reacted with aryl iodide in the presence of CO to give the corresponding S-aryl thioesters.

Palladium-catalyzed carbonylative transformation of aryl iodides and sulfonyl chlorides: convenient access to thioesters

2020 ◽  
Vol 7 (6) ◽  
pp. 885-889 ◽  
Author(s):  
Xinxin Qi ◽  
Zhi-Peng Bao ◽  
Xiao-Feng Wu
Keyword(s):  
Sulfonyl Chlorides ◽  
Aryl Iodides ◽  
Palladium Catalyzed ◽  
Convenient Access

A palladium-catalyzed carbonylative transformation of aryl iodides and sulfonyl chlorides to thioesters has been studied.

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