scholarly journals Palladium/Copper Dual Catalysis for the Cross‐Coupling of Aryl(trialkyl)silanes with Aryl Bromides

2018 ◽  
Vol 57 (7) ◽  
pp. 1987-1990 ◽  
Author(s):  
Takeshi Komiyama ◽  
Yasunori Minami ◽  
Yuki Furuya ◽  
Tamejiro Hiyama
Keyword(s):  
Cross Coupling ◽  
Aryl Bromides ◽  
The Cross ◽  
Dual Catalysis

scholarly journals Palladium/Copper Dual Catalysis for the Cross‐Coupling of Aryl(trialkyl)silanes with Aryl Bromides

2018 ◽  
Vol 130 (7) ◽  
pp. 2005-2008 ◽  
Author(s):  
Takeshi Komiyama ◽  
Yasunori Minami ◽  
Yuki Furuya ◽  
Tamejiro Hiyama
Keyword(s):  
Cross Coupling ◽  
Aryl Bromides ◽  
The Cross ◽  
Dual Catalysis

scholarly journals Recent Progress in the Cross-Coupling Reaction Using Triorgano­silyl-Type Reagents

Synlett ◽  
2017 ◽  
Vol 28 (15) ◽  
pp. 1873-1884 ◽  
Author(s):  
Yasunori Minami ◽  
Tamejiro Hiyama ◽  
Takeshi Komiyama
Keyword(s):  
Recent Progress ◽  
Coupling Reaction ◽  
Cross Coupling ◽  
Aryl Halides ◽  
Organosilicon Compounds ◽  
Aryl Bromides ◽  
Cross Coupling Reaction ◽  
The Cross ◽  
Silicon Based ◽  
Coupling Polymerization

The silicon-based cross-coupling reaction has attracted much attention over recent decades because there are many advantages in using organosilicon compounds. However, the use of reagents with a triorganosilyl group as a key function remains to be established. This account summarizes our recent progress in cross-coupling chemistry with such silyl reagents.1 Introduction2 Preparation of HOMSi Reagents from Aryl Bromides and Disilanes3 HOMSi Reagents from Heteroaromatics and Hydrosilanes4 Cross-Coupling Polymerization with HOMSi Reagents5 Cross-Coupling with Aryl(triethyl)silanes6 Amination of Aryl Halides with N-TMS-Amines7 Conclusion and Perspective

scholarly journals C(sp3)–C(sp2) cross-coupling of alkylsilicates with borylated aryl bromides – an iterative platform to alkylated aryl- and heteroaryl boronates

2017 ◽  
Vol 8 (1) ◽  
pp. 530-535 ◽  
Author(s):  
Brandon A. Vara ◽  
Matthieu Jouffroy ◽  
Gary A. Molander
Keyword(s):  
Cross Coupling ◽  
Aryl Bromides ◽  
Dual Catalysis

Primary and secondary ammonium alkylsilicates undergo facile C(sp3)–C(sp2) cross-coupling with borylated aryl bromides under mild photoredox/nickel dual catalysis conditions.

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

2018 ◽  
Vol 20 (3) ◽  
pp. 760-763 ◽  
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

Concise Synthesis of GB22 by Endo-Selective Siloxycyclopropane Arylation

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>

Concise Synthesis of GB22 by Endo-Selective Siloxycyclopropane Arylation

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>

Monodentate Trialkylphosphines: Privileged Ligands in Metal-catalyzed Crosscoupling Reactions

2020 ◽  
Vol 24 (3) ◽  
pp. 231-264 ◽  
Author(s):  
Kevin H. Shaughnessy
Keyword(s):  
Transition Metal ◽  
Cross Coupling ◽  
Coupling Reactions ◽  
Cross Coupling Reactions ◽  
Aryl Bromides ◽  
Wide Range ◽  
Sterically Demanding ◽  
Transition Metal Catalyzed ◽  
Catalyzed Reactions ◽  
Metal Catalyzed

Phosphines are widely used ligands in transition metal-catalyzed reactions. Arylphosphines, such as triphenylphosphine, were among the first phosphines to show broad utility in catalysis. Beginning in the late 1990s, sterically demanding and electronrich trialkylphosphines began to receive attention as supporting ligands. These ligands were found to be particularly effective at promoting oxidative addition in cross-coupling of aryl halides. With electron-rich, sterically demanding ligands, such as tri-tertbutylphosphine, coupling of aryl bromides could be achieved at room temperature. More importantly, the less reactive, but more broadly available, aryl chlorides became accessible substrates. Tri-tert-butylphosphine has become a privileged ligand that has found application in a wide range of late transition-metal catalyzed coupling reactions. This success has led to the use of numerous monodentate trialkylphosphines in cross-coupling reactions. This review will discuss the general properties and features of monodentate trialkylphosphines and their application in cross-coupling reactions of C–X and C–H bonds.

Sign in / Sign up

Export Citation Format

Share Document