Synthesis 2020; 52(21): 3153-3161
DOI: 10.1055/s-0040-1707175
psp
© Georg Thieme Verlag Stuttgart · New York

Remote Deprotometalation-Iodolysis of N,N-Diisopropyl-2-trimethylsilylferrocenecarboxamide: A New Route Toward 1,1′-Disubstituted Ferrocenes

Lingaswamy Kadari
a  Univ Rennes, CNRS, ISCR (Institut des Sciences Chimiques de Rennes)-UMR 6226, 35000 Rennes, France   Email: [email protected]
b  Organic Synthesis and Process Chemistry Division, CSIR-Indian Institute of Chemical Technology, Hyderabad 500007, India   Email: [email protected]
,
Thierry Roisnel
a  Univ Rennes, CNRS, ISCR (Institut des Sciences Chimiques de Rennes)-UMR 6226, 35000 Rennes, France   Email: [email protected]
,
a  Univ Rennes, CNRS, ISCR (Institut des Sciences Chimiques de Rennes)-UMR 6226, 35000 Rennes, France   Email: [email protected]
,
b  Organic Synthesis and Process Chemistry Division, CSIR-Indian Institute of Chemical Technology, Hyderabad 500007, India   Email: [email protected]
,
Florence Mongin
a  Univ Rennes, CNRS, ISCR (Institut des Sciences Chimiques de Rennes)-UMR 6226, 35000 Rennes, France   Email: [email protected]
› Author Affiliations
This work was supported by the Université de Rennes 1 and CNRS.
Further Information

Publication History

Received: 19 May 2020

Accepted after revision: 08 June 2020

Publication Date:
01 July 2020 (online)


Abstract

The 1,1′-disubstitution is currently the most frequent substitution pattern encountered in the ferrocene series. Here an original access based on the remote deprotometalation of N,N-diisopropyl-2-trimethylsilylferrocenecarboxamide is reported. The key intermediate, 1′-iodo-N,N-diisopropylferrocenecarboxamide, was prepared in multiple grams and was further functionalized toward fifteen 1′-substituted iodoferrocenes.

Supporting Information

 
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