Identifying the Roles of Amino Acids, Alcohols and 1,2-Diamines as Mediators in Coupling of Haloarenes to Arenes | Zendy

Shengze Zhou | Zendy; Eswararao Doni | Zendy; G. M. Anderson | Zendy; Ryan G. Kane | Zendy; S. MacDougall | Zendy; V. Ironmonger | Zendy; Tell Tuttle | Zendy; John A. Murphy | Zendy

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Identifying the Roles of Amino Acids, Alcohols and 1,2-Diamines as Mediators in Coupling of Haloarenes to Arenes

Author(s) -

Shengze Zhou,

Eswararao Doni,

G. M. Anderson,

Ryan G. Kane,

S. MacDougall,

V. Ironmonger,

Tell Tuttle,

John A. Murphy

Publication year - 2014

Publication title -

journal of the american chemical society

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 7.115

H-Index - 612

eISSN - 1520-5126

pISSN - 0002-7863

DOI - 10.1021/ja5101036

Subject(s) - chemistry , reactivity (psychology) , organic chemistry , coupling (piping) , coupling reaction , medicinal chemistry , catalysis , medicine , mechanical engineering , alternative medicine , pathology , engineering

Coupling of haloarenes to arenes has been facilitated by a diverse range of organic additives in the presence of KO(t)Bu or NaO(t)Bu since the first report in 2008. Very recently, we showed that the reactivity of some of these additives (e.g., compounds 6 and 7) could be explained by the formation of organic electron donors in situ, but the role of other additives was not addressed. The simplest of these, alcohols, including 1,2-diols, 1,2-diamines, and amino acids are the most intriguing, and we now report experiments that support their roles as precursors of organic electron donors, underlining the importance of this mode of initiation in these coupling reactions.

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