Sterically Controlled Cu-Catalyzed or Transition-Metal-Free Cross-Coupling of gem-Difluoroalkenes with Tertiary, Secondary, and Primary Alkyl Grignard Reagents

2016 ◽  
Vol 18 (17) ◽  
pp. 4284-4287 ◽  
Author(s):  
Wenpeng Dai ◽  
Hongyan Shi ◽  
Xianghu Zhao ◽  
Song Cao
Keyword(s):  
Transition Metal ◽  
Cross Coupling ◽  
Grignard Reagents ◽  
Metal Free

Transition-Metal-Free Desulfinative Cross-Coupling of Heteroaryl Sulfinates with Grignard Reagents

2019 ◽  
Vol 21 (4) ◽  
pp. 937-940 ◽  
Author(s):  
Jun Wei ◽  
Huamin Liang ◽  
Chuanfa Ni ◽  
Rong Sheng ◽  
Jinbo Hu
Keyword(s):  
Transition Metal ◽  
Cross Coupling ◽  
Grignard Reagents ◽  
Metal Free

scholarly journals Improved Synthesis of Icosahedral Carboranes Containing Exohedral B–c and C–c Bonds

2018 ◽  
Author(s):  
Kierstyn P. Anderson ◽  
Harrison A. Mills ◽  
Chantel Mao ◽  
Kent O. Kirlikovali ◽  
Jonathan C. Axtell ◽  
...  
Keyword(s):  
Transition Metal ◽  
Cross Coupling ◽  
Phosphine Ligand ◽  
Grignard Reagents ◽  
Boron Clusters ◽  
Metal Free ◽  
Selective Substitution ◽  
Improved Methods ◽  
Carbon Based

<table><tr><td><p>We report improved methods utilizing orthogonal chemistry to achieve efficient substitution at electron-rich B-vertices and electron-poor C-vertices of carborane. Functionalization of B-vertices with alkyl and (hetero)aryl groups using corresponding Grignard reagents has been improved by the use of a Pd-based precatalyst featuring an electron-rich biaryl phosphine ligand. Using the developed catalytic conditions lead to cross-coupling transformations achieved within several hours. Importantly, this method is applicable towards alkyl-based Grignard reagents containing β-hydrogens. Additionally, transition metal-free substitution of (hetero)aryl substrates on C-vertices was developed under S<sub>N</sub>Ar conditions. The selective substitution of carboranes afforded by these methods holds potential for the rational synthesis of heterofunctionalized boron clusters with substituents on both boron and carbon-based vertices.</p></td></tr></table>

scholarly journals Improved Synthesis of Icosahedral Carboranes Containing Exohedral B–c and C–c Bonds

2018 ◽  
Author(s):  
Kierstyn P. Anderson ◽  
Harrison A. Mills ◽  
Chantel Mao ◽  
Kent O. Kirlikovali ◽  
Jonathan C. Axtell ◽  
...  
Keyword(s):  
Transition Metal ◽  
Cross Coupling ◽  
Phosphine Ligand ◽  
Grignard Reagents ◽  
Boron Clusters ◽  
Metal Free ◽  
Selective Substitution ◽  
Improved Methods ◽  
Carbon Based

<table><tr><td><p>We report improved methods utilizing orthogonal chemistry to achieve efficient substitution at electron-rich B-vertices and electron-poor C-vertices of carborane. Functionalization of B-vertices with alkyl and (hetero)aryl groups using corresponding Grignard reagents has been improved by the use of a Pd-based precatalyst featuring an electron-rich biaryl phosphine ligand. Using the developed catalytic conditions lead to cross-coupling transformations achieved within several hours. Importantly, this method is applicable towards alkyl-based Grignard reagents containing β-hydrogens. Additionally, transition metal-free substitution of (hetero)aryl substrates on C-vertices was developed under S<sub>N</sub>Ar conditions. The selective substitution of carboranes afforded by these methods holds potential for the rational synthesis of heterofunctionalized boron clusters with substituents on both boron and carbon-based vertices.</p></td></tr></table>

scholarly journals Transition-Metal-Free Cross-Coupling of Aryl Halides with Arylstannanes

2021 ◽  
Author(s):  
Qing He ◽  
Wenli Wang ◽  
Yong Liang ◽  
Zunting Zhang ◽  
Stanislaw F. Wnuk
Keyword(s):  
Transition Metal ◽  
Cross Coupling ◽  
Aryl Halides ◽  
Metal Free

ChemInform Abstract: A Transition-Metal-Free Cross-Coupling Reaction of Allylic Bromides with Aryl- and Vinylboronic Acids.

ChemInform ◽  
2012 ◽  
Vol 43 (33) ◽  
pp. no-no
Author(s):  
Mitsuhiro Ueda ◽  
Kota Nishimura ◽  
Ryo Kashima ◽  
Ilhyong Ryu
Keyword(s):  
Transition Metal ◽  
Coupling Reaction ◽  
Cross Coupling ◽  
Metal Free ◽  
Cross Coupling Reaction
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