Regioselective Iodine/Zinc-Exchange for the Selective Functionalization of Polyiodinated Arenes and Heterocycles in Toluene

Synthesis ◽  
2021 ◽  
Author(s):  
Florian Sanchez ◽  
Alexandre Desaintjean ◽  
Fanny Danton ◽  
Paul Knochel
Keyword(s):  
Exchange Reactions ◽  
Acyl Chlorides ◽  
Selective Functionalization ◽  
Aryl Iodides

Regioselective I/Zn-exchange reactions were performed on polyiodinated arenes or heterocycles within 20 min at 0-25 °C using the bimetallic combination pTol2Zn·2LiOR (R = (CH2)2N(Me)(CH2)2NMe2) in toluene. The resulting diaryl- or di(hetero)aryl-zincs reacted well with allylic bromides and acyl chlorides to provide functionalized (hetero)aryl iodides in good yields.

Preparation of Functionalized Diorganomagnesium Reagents in Toluene via Bromine or Iodine/Magnesium-Exchange Reactions

Synthesis ◽  
2021 ◽  
Author(s):  
Alexandre Desaintjean ◽  
Fanny Danton ◽  
Paul Knochel
Keyword(s):  
Exchange Reaction ◽  
Nitro Group ◽  
General Formula ◽  
Functional Groups ◽  
Exchange Reactions ◽  
Acyl Chlorides ◽  
Aryl Iodides ◽  
Highly Sensitive ◽  
Wide Range ◽  
Magnesium Exchange

A wide range of polyfunctionalized di(hetero)aryl- and dialkenyl-magnesium reagents were prepared in toluene within 10 to 120 min between −78 °C and 25 °C via an I/Mg- or Br/Mg-exchange reaction using reagents of the general formula R2Mg (R = sBu, Mes). Highly sensitive functional groups, such as a triazene or a nitro group, were tolerated in these exchange reactions, enabling the synthesis of various functionalized (hetero)arenes and alkenes derivatives after quenching with several electrophiles including allyl bromides, acyl chlorides, aldehydes, ketones, and aryl iodides.

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.

Palladium/Copper (I) halide-cocatalyzed stereospecific coupling of 1-fluorovinylstannanes with aryl iodides and acyl chlorides

1997 ◽  
Vol 38 (44) ◽  
pp. 7677-7680 ◽  
Author(s):  
Chen Chen ◽  
Keith Wilcoxen ◽  
Kyung-il Kim ◽  
James R. McCarthy
Keyword(s):  
Acyl Chlorides ◽  
Aryl Iodides

Successive Iodine−Magnesium or −Copper Exchange Reactions for the Selective Functionalization of Polyhalogenated Aromatics

2003 ◽  
Vol 5 (8) ◽  
pp. 1229-1231 ◽  
Author(s):  
Xiaoyin Yang ◽  
Thomas Rotter ◽  
Claudia Piazza ◽  
Paul Knochel
Keyword(s):  
Exchange Reactions ◽  
Selective Functionalization ◽  
Copper Exchange

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.

Exchange reactions and electrolytic dissociation

1948 ◽  
Vol 45 ◽  
pp. 147-149 ◽  
Author(s):  
C. C. Evans ◽  
S. Sugden
Keyword(s):  
Exchange Reactions ◽  
Electrolytic Dissociation
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