The Cobalt-Catalyzed Cross-Coupling Reaction of Alkyl Halides with Alkyl Grignard Reagents: A New Route to Constructing Quaternary Carbon Centers­

Takanori Iwasaki; Hiroaki Takagawa; Kanako Okamoto; Surya Prakash Singh; Hitoshi Kuniyasu; Nobuaki Kambe

doi:10.1055/s-0033-1341152

Synthesis, Inhaltsverzeichnis

Synthesis 2014; 46(12): 1583-1592
DOI: 10.1055/s-0033-1341152

practical synthetic procedures

The Cobalt-Catalyzed Cross-Coupling Reaction of Alkyl Halides with Alkyl Grignard Reagents: A New Route to Constructing Quaternary Carbon Centers

Takanori Iwasaki

^aDepartment of Applied Chemistry, Graduate School of Engineering, Osaka University, Suita, Osaka 565-0871, Japan Fax: +81(6)68797390 eMail: kambe@chem.eng.osaka-u.ac.jp

,

Hiroaki Takagawa

^aDepartment of Applied Chemistry, Graduate School of Engineering, Osaka University, Suita, Osaka 565-0871, Japan Fax: +81(6)68797390 eMail: kambe@chem.eng.osaka-u.ac.jp

,

Kanako Okamoto

^aDepartment of Applied Chemistry, Graduate School of Engineering, Osaka University, Suita, Osaka 565-0871, Japan Fax: +81(6)68797390 eMail: kambe@chem.eng.osaka-u.ac.jp

,

Surya Prakash Singh

^bInorganic and Physical Chemistry Division, CSIR–Indian Institute of Chemical Technology, Tarnaka, Hyderabad 500607, India

,

Hitoshi Kuniyasu

^aDepartment of Applied Chemistry, Graduate School of Engineering, Osaka University, Suita, Osaka 565-0871, Japan Fax: +81(6)68797390 eMail: kambe@chem.eng.osaka-u.ac.jp

,

Nobuaki Kambe*

^aDepartment of Applied Chemistry, Graduate School of Engineering, Osaka University, Suita, Osaka 565-0871, Japan Fax: +81(6)68797390 eMail: kambe@chem.eng.osaka-u.ac.jp

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Abstract

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Abstract

The cross-coupling of alkyl (pseudo)halides with alkyl Grignard reagents is catalyzed efficiently by a cobalt(II) chloride–lithium iodide–1,3-diene catalytic system, which provides a new synthetic tool for constructing sp³ carbon chains. This system is particularly useful for creating quaternary carbon centers via the use of tertiary alkyl Grignard reagents. Various functional groups including esters, amides and carbamates are well tolerated.

Key words

cobalt - cross-coupling - Grignard reagents - alkyl halides - quaternary carbon

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Referenzen

References

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The Cobalt-Catalyzed Cross-Coupling Reaction of Alkyl Halides with Alkyl Grignard Reagents: A New Route to Constructing Quaternary Carbon Centers­

The Cobalt-Catalyzed Cross-Coupling Reaction of Alkyl Halides with Alkyl Grignard Reagents: A New Route to Constructing Quaternary Carbon Centers