Negishi coupling reactions with [11C]CH3I: a versatile method for efficient 11C-C bond formation

被引：6

作者：

Rejc, Luka ^{[1
]}

Gomez-Vallejo, Vanessa ^{[1
]}

Alcazar, Jesus ^{[2
]}

Alonso, Nerea ^{[2
]}

Ignacio Andres, Jose ^{[2
]}

Arrieta, Ana ^{[3
]}

Cossio, Fernando P. ^{[3
]}

Llop, Jordi ^{[1
]}

机构：

[1] CIC biomaGUNE, Radiochem & Nucl Imaging, Paseo Miramon 182, San Sebastian 20014, Guipuzcoa, Spain

[2] Janssen Res & Dev, Lead Discovery Chem Discovery Sci, Jarama 75A, Toledo 45007, Spain

[3] Univ Basque Country, UPV EHU, ORFEO CINQA, Dept Organ Chem 1,DIPC, Paseo Manuel Lardizabal 3, San Sebastian 20018, Spain

来源：

CHEMICAL COMMUNICATIONS | 2018年 / 54卷 / 35期

关键词：

ORGANOZINC HALIDES; MECHANISM; ZNMECL;

D O I：

10.1039/c8cc01540f

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Herein, we present a fast, efficient and general one-pot method for the synthesis of C-11-labelled compounds via the Negishi cross-coupling reaction. Our approach, based on the in situ formation of [C-11]CH3ZnI and subsequent reaction with aryl halides or triflates, has proven efficient to synthesize [C-11]thymidine, a biologically relevant compound with potential applications as a proliferation marker. Theoretical calculations have shown irreversible formation of a tetracoordinated nucleophilic C-11-Zn(II) reagent and electronic requirements for an efficient Negishi coupling.

引用

页码：4398 / 4401

页数：4

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