Retraction of “Heterogeneous Titania-Photoredox/Nickel Dual Catalysis: Decarboxylative Cross-Coupling of Carboxylic Acids with Aryl Iodides”

Christopher D. McTiernan; Xavier Leblanc; Juan C. Scaiano

doi:10.1021/acscatal.8b03510

Heterogeneous Titania-Photoredox/Nickel Dual Catalysis: Decarboxylative Cross-Coupling of Carboxylic Acids with Aryl Iodides

ACS Catalysis ◽

10.1021/acscatal.6b03687 ◽

2017 ◽

Vol 7 (3) ◽

pp. 2171-2175 ◽

Cited By ~ 24

Author(s):

Christopher D. McTiernan ◽

Xavier Leblanc ◽

Juan C. Scaiano

Keyword(s):

Carboxylic Acids ◽

Cross Coupling ◽

Aryl Iodides ◽

Dual Catalysis

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Nickel-Catalyzed 1,2-Diarylation of Alkenyl Carboxylates: A Gateway to 1,2,3-Trifunctionalized Building Blocks

10.26434/chemrxiv.9900980 ◽

2019 ◽

Author(s):

Joseph Derosa ◽

Taeho Kang ◽

Van Tran ◽

Steven Wisniewski ◽

Malkanthi Karunananda ◽

...

Keyword(s):

Carboxylic Acids ◽

Functional Group ◽

Cross Coupling ◽

Building Blocks ◽

Step Count ◽

Bioactive Molecules ◽

Aryl Iodides ◽

Boronic Esters ◽

Synthetic Utility

A nickel-catalyzed conjunctive cross-coupling of alkenyl carboxylic acids, aryl iodides, and aryl/alkenyl boronic esters is reported. The reaction delivers the desired 1,2-diarylated and 1,2-arylalkenylated products with excellent regiocontrol. To demonstrate the synthetic utility of the method, a representative product is prepared on gram scale and then diversified to eight 1,2,3-trifunctionalized building blocks using two-electron and one-electron logic. Using this method, three routes toward bioactive molecules are improved in terms of yield and/or step count. This method represents the first example of catalytic 1,2-diarylation of an alkene directed by a native carboxylate functional group.

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Visible-Light Photoredox/Nickel Dual Catalysis for the Cross-Coupling of Sulfinic Acid Salts with Aryl Iodides

Organic Letters ◽

10.1021/acs.orglett.7b03896 ◽

2018 ◽

Vol 20 (3) ◽

pp. 760-763 ◽

Cited By ~ 32

Author(s):

Nai-Wei Liu ◽

Kamil Hofman ◽

André Herbert ◽

Georg Manolikakes

Keyword(s):

Visible Light ◽

Cross Coupling ◽

Sulfinic Acid ◽

Aryl Iodides ◽

The Cross ◽

Dual Catalysis ◽

Acid Salts

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Nickel-Catalyzed 1,2-Diarylation of Alkenyl Carboxylates: A Gateway to 1,2,3-Trifunctionalized Building Blocks

10.26434/chemrxiv.9900980.v1 ◽

2019 ◽

Author(s):

Joseph Derosa ◽

Taeho Kang ◽

Van Tran ◽

Steven Wisniewski ◽

Malkanthi Karunananda ◽

...

Keyword(s):

Carboxylic Acids ◽

Functional Group ◽

Cross Coupling ◽

Building Blocks ◽

Step Count ◽

Bioactive Molecules ◽

Aryl Iodides ◽

Boronic Esters ◽

Synthetic Utility

A nickel-catalyzed conjunctive cross-coupling of alkenyl carboxylic acids, aryl iodides, and aryl/alkenyl boronic esters is reported. The reaction delivers the desired 1,2-diarylated and 1,2-arylalkenylated products with excellent regiocontrol. To demonstrate the synthetic utility of the method, a representative product is prepared on gram scale and then diversified to eight 1,2,3-trifunctionalized building blocks using two-electron and one-electron logic. Using this method, three routes toward bioactive molecules are improved in terms of yield and/or step count. This method represents the first example of catalytic 1,2-diarylation of an alkene directed by a native carboxylate functional group.

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Concise Synthesis of GB22 by Endo-Selective Siloxycyclopropane Arylation

10.26434/chemrxiv.8263415.v1 ◽

2019 ◽

Cited By ~ 3

Author(s):

Hannah E. Burdge ◽

Takuya Oguma ◽

Takahiro Kawajiri ◽

Ryan Shenvi

Keyword(s):

Intramolecular Cyclization ◽

Cross Coupling ◽

Building Blocks ◽

Ring Expansion ◽

Dual Catalysis ◽

Acid Labile

<div><div><div><p>The first synthesis of GB22 was accomplished by a con- cise, modular route. Two building blocks converged in a novel sp3-sp2 attached-ring coupling that used Ir/Ni dual-catalysis to reverse the regioselectivity of siloxycy- clopropane arylation. This cross-coupling proved general to access β-substituted tetralones via ring-expansion of indanone-derived siloxycyclopropanes. The congested, bridging rings of the GB alkaloids were completed using an aluminum-HFIP complex that effected intramolecular cyclization of an acid-labile substrate.</p></div></div></div>

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Concise Synthesis of GB22 by Endo-Selective Siloxycyclopropane Arylation

10.26434/chemrxiv.8263415 ◽

2019 ◽

Author(s):

Hannah E. Burdge ◽

Takuya Oguma ◽

Takahiro Kawajiri ◽

Ryan Shenvi

Keyword(s):

Intramolecular Cyclization ◽

Cross Coupling ◽

Building Blocks ◽

Ring Expansion ◽

Dual Catalysis ◽

Acid Labile

<div><div><div><p>The first synthesis of GB22 was accomplished by a con- cise, modular route. Two building blocks converged in a novel sp3-sp2 attached-ring coupling that used Ir/Ni dual-catalysis to reverse the regioselectivity of siloxycy- clopropane arylation. This cross-coupling proved general to access β-substituted tetralones via ring-expansion of indanone-derived siloxycyclopropanes. The congested, bridging rings of the GB alkaloids were completed using an aluminum-HFIP complex that effected intramolecular cyclization of an acid-labile substrate.</p></div></div></div>

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Nickel-Catalyzed Asymmetric Reductive Cross-Coupling of α-Chloroesters with (Hetero)Aryl Iodides

Chemical Science ◽

10.1039/d1sc00822f ◽

2021 ◽

Author(s):

Travis DeLano ◽

Sara Dibrell ◽

Caitlin R. Lacker ◽

Adam Pancoast ◽

Kelsey Poremba ◽

...

Keyword(s):

Cross Coupling ◽

Mild Conditions ◽

Aryl Iodides ◽

Reaction Proceeds

An asymmetric reductive cross-coupling of α-chloroesters and (hetero)aryl iodides is reported. This nickel-catalyzed reaction proceeds with a chiral BiOX ligand under mild conditions, affording α-arylesters in good yields and enantioselectivities....

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