Generation of cycloheptynes and cyclooctynes via a sulfoxide–magnesium exchange reaction of readily synthesized 2-sulfinylcycloalkenyl triflates

2015 ◽  
Vol 51 (42) ◽  
pp. 8745-8748 ◽  
Author(s):  
Suguru Yoshida ◽  
Fumika Karaki ◽  
Keisuke Uchida ◽  
Takamitsu Hosoya
Keyword(s):  
Exchange Reaction ◽  
Magnesium Exchange

Cycloheptynes and cyclooctynes have been efficiently generated via a sulfoxide–magnesium exchange reaction of readily synthesized 2-sulfinylcycloalkenyl triflates.

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.

Direct preparation of polyfunctional amino-substituted arylmagnesium reagents via an iodine–magnesium exchange reaction

2003 ◽  
pp. 396-397 ◽  
Author(s):  
Greta Varchi ◽  
Christiane Kofink ◽  
David M. Lindsay ◽  
Alfredo Ricci ◽  
Paul Knochel
Keyword(s):  
Exchange Reaction ◽  
Direct Preparation ◽  
Magnesium Exchange

scholarly journals Facile Synthesis of Phthalides from Methyl ortho-Iodobenzoates and Ketones via an Iodine–Magnesium Exchange Reaction Using a Silylmethyl Grignard Reagent

2017 ◽  
Vol 46 (6) ◽  
pp. 858-861 ◽  
Author(s):  
Yu Nakamura ◽  
Suguru Yoshida ◽  
Takamitsu Hosoya
Keyword(s):  
Exchange Reaction ◽  
Grignard Reagent ◽  
Facile Synthesis ◽  
Magnesium Exchange

Tributylmagnesium ate complex-mediated novel bromine–magnesium exchange reaction for selective monosubstitution of dibromoarenes

2001 ◽  
Vol 42 (29) ◽  
pp. 4841-4844 ◽  
Author(s):  
Takehiko Iida ◽  
Toshihiro Wada ◽  
Koji Tomimoto ◽  
Toshiaki Mase
Keyword(s):  
Exchange Reaction ◽  
Magnesium Exchange

ChemInform Abstract: Selective Halogen-Magnesium Exchange Reaction via Organomagnesium Ate Complex.

ChemInform ◽  
2010 ◽  
Vol 32 (41) ◽  
pp. no-no
Author(s):  
Atsushi Inoue ◽  
Kazuya Kitagawa ◽  
Hiroshi Shinokubo ◽  
Koichiro Oshima
Keyword(s):  
Exchange Reaction ◽  
Magnesium Exchange

New Stereoselective Preparation of (Z)-3-Perfluoroalkyl-3-magnesiated Enoates by an Iodine−Magnesium Exchange Reaction

2004 ◽  
Vol 69 (12) ◽  
pp. 4262-4264 ◽  
Author(s):  
Jérôme Thibonnet ◽  
Alain Duchêne ◽  
Jean-Luc Parrain ◽  
Mohamed Abarbri
Keyword(s):  
Exchange Reaction ◽  
Magnesium Exchange

ChemInform Abstract: Generation of Cycloheptynes and Cyclooctynes via a Sulfoxide-Magnesium Exchange Reaction of Readily Synthesized 2-Sulfinylcycloalkenyl Triflates.

ChemInform ◽  
2015 ◽  
Vol 46 (39) ◽  
pp. no-no
Author(s):  
Suguru Yoshida ◽  
Fumika Karaki ◽  
Keisuke Uchida ◽  
Takamitsu Hosoya
Keyword(s):  
Exchange Reaction ◽  
Magnesium Exchange

ChemInform Abstract: Stereoselective Preparation of Functionalized Alkenylmagnesium Reagents via a Iodine-Magnesium Exchange Reaction.

ChemInform ◽  
2010 ◽  
Vol 30 (29) ◽  
pp. no-no
Author(s):  
Mario Rottlaender ◽  
Laure Boymond ◽  
Gerard Cahiez ◽  
Paul Knochel
Keyword(s):  
Exchange Reaction ◽  
Magnesium Exchange

Stereoselective preparation of highly functionalized (Z)-3-magnesiated enoates by an iodine–magnesium exchange reaction

2001 ◽  
pp. 2068-2069 ◽  
Author(s):  
Ioannis Sapountzis ◽  
Wolfgang Dohle ◽  
Paul Knochel
Keyword(s):  
Exchange Reaction ◽  
Magnesium Exchange

scholarly journals Fritsch–Buttenberg–Wiechell rearrangement of magnesium alkylidene carbenoids leading to the formation of alkynes

2021 ◽  
Vol 17 ◽  
pp. 1352-1359
Author(s):  
Tsutomu Kimura ◽  
Koto Sekiguchi ◽  
Akane Ando ◽  
Aki Imafuji
Keyword(s):  
Dft Calculations ◽  
Exchange Reaction ◽  
Carbonyl Compounds ◽  
Organometallic Reagents ◽  
Magnesium Exchange

A series of 1-heteroatom-substituted vinyl p-tolyl sulfoxides were prepared and treated with organometallic reagents to evaluate which combination of sulfoxides and organometallic reagents yielded alkynes the most efficiently. The use of 1-chlorovinyl p-tolyl sulfoxide and isopropylmagnesium chloride was optimal for this purpose. A variety of 1-chlorovinyl p-tolyl sulfoxides were prepared from carbonyl compounds and chloromethyl p-tolyl sulfoxide and were converted into alkynes via the sulfoxide/magnesium exchange reaction and subsequent Fritsch–Buttenberg–Wiechell (FBW) rearrangement of the resulting magnesium alkylidene carbenoids. The mechanism of the FBW rearrangement of magnesium alkylidene carbenoids was studied by using 13C-labeled sulfoxides and by using DFT calculations.

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