aromatic finkelstein reaction

Published by on November 13, 2020

In this communication, we report the superior role of 1,3-dimethyl-2-imidazolidinone (DMI) as a solvent for aromatic Finkelstein iodination (AFI), the conversion of aryl bromides to aryl iodides. it in a third party non-RSC publication you must 167 0 obj <> endobj Aromatic Finkelstein reaction has to be well catalyzed by copper iodide along with diamine ligands as these reactions don’t occur easily. Our findings for AFI avoid the use of toxic solvents such as N,N-dimethylformamide and hexamethylphosphoramide. Go to our of the whole article in a thesis or dissertation. Copper-Catalyzed Halogen Exchange in Aryl Halides: An Aromatic Finkelstein Reaction Klapars, A.; Buchwald, S. L. ?����`B��i)���${�*��]v$�P@/�[(��!$t%reR(��J\A�O��< ��! Authors contributing to RSC publications (journal articles, books or book chapters) If you are the author of this article you do not need to formally request permission Department of Chemistry, Imperial College London, South Kensington, London, UK ��1��l��33`~���\N��:��S��B堺��Q^R$�@��;��n?-�i�A]��� �]�TL��f�X�`��Ob����4J׾� Here's the correct one, as well as the full article. The transformation was found to be general for a wide range of substrates and was used for the synthesis of iodo-PK11195, an imaging agent of Alzheimer's disease and iniparib, a … It is an organic reaction that uses an alkyl halide exchange into another alkyl halide through a reaction wherein the metal halide salt is used. This may take some time to load. Copper-catalysed aromatic-Finkelstein reactions with amine-based ligand systems X. Jin and R. P. Davies, Catal. Please enable JavaScript h�b```f``��^;@��9Vy0D����?�K�-�`�K�� �I�� XX is the XXth reference in the list of references. Apart from CuI, nickel bromide and tri-n-butylphosphine are also suitable catalysts for aromatic Finkelstein reaction. In all cases the Ref. Aromatic Finkelstein Reaction. This copper(II) complex was also shown to be catalytically active in the halogen exchange reaction. r.davies@imperial.ac.uk. * �ݙN��*�ܒ��������Š��8\����[���C�!j����C��w��K�g��������`���ĥuM���hU?�m���BV{���Y^id����*��`1�Y,���� Other catalysts like nickel bromide and n-butyl phosphine can also be used. Finkelstein Reaction Vinyl, aryl and tertiary alkyl halides are unreactive. To learn about our use of cookies and how you can manage your cookie settings, please see our Cookie Policy. For reproduction of material from all other RSC journals and books: For reproduction of material from all other RSC journals. %%EOF In this communication, we report the superior role of 1,3-dimethyl-2-imidazolidinone (DMI) as a solvent for aromatic Finkelstein iodination (AFI), the conversion of aryl bromides to aryl iodides. formally request permission using Copyright Clearance Center. Accepted author version posted online: 30 Jun 2011, Register to receive personalised research and resources by email, An International Journal for Rapid Communication of Synthetic Organic Chemistry, Facile Aromatic Finkelstein Iodination (AFI) Reaction in 1,3-Dimethyl-2-imidazolidinone (DMI), Department of Chemistry , Graduate School of Science and Engineering, Tokyo Metropolitan University , Tokyo , Japan, /doi/full/10.1080/00397911.2010.523152?needAccess=true. �=����?������� ����᰹K�o6�Cx���ܓ_J����}?��jr�l����dOf��'��O9�V�\ßw8b "��[�ێ��x�~�^�X aE��h���Y ��,��`ƈ��g�t2��(���o����J8�z+{m��b5~��Ҏ��Gc��G��5|�@:5����mz qr�)�X���O��"����*7�� � �%(�����0����/~����Q��J��oәR�L���j�$� 3>��t1�>9�*�� ��>�Ш�B&Q�3y��a�����\�%H�Ì尢|������^��T���� L%� �=�]�LzG����!��d���Y�CR�)�)J����� �1#��C�P(J�B���%~6`K�+A�B0��+��V��v��n~]3���dv>37!�K4��/#K��ZE^�L�� ��0`�*Ӆ�$���B@���Kt'��9�*m���87L*ײ7,8��g��� ޡ{�ә����������T���&�z�S0�����O�C6ըe�d���?WS0��pþ��a-4�)Ka}ĂC�_g��75�N1 htVU-`:� nXC�ΰG �e�,b �֐' ��ȹ�d^�qX�2�St�9���]������o��q� ��\��.1��A��(ښ���; �X*���j to reproduce figures, diagrams etc. <>/Metadata 684 0 R/ViewerPreferences 685 0 R>> In contrast to earlier methods, the use of inert atmosphere conditions was not required to obtain high yields and purity. Aromatic Finkelstein reaction has to be well catalyzed by copper iodide along with diamine ligands as these reactions don’t occur easily. The reaction is dependent upon nature of group whether it is a good leaving group or not, nucleophilicity, alkyl halide reactivity, and carbon-halide bond. The Scope of the Copper-Catalyzed Conversion of Aryl Bromides into Aryl Iodides a a Isolated yields (average of two runs); >95% purity is available on our Permission Requests page. article provided that the correct acknowledgement is given with the reproduced material. endstream endobj startxref This work was supported in part by Grants-in-Aid for Scientific Research (Category B: 08091971 and Priority Areas: 08071557 to K.-I. (N,�iV�'V͆�������k_ xq��p��fw�o#���"$fxDҞr�O�\���"_O�%MM�kAT=�H�l��k�z���) ��0�yK��A����c����8a>�%ܑ|{��('�q�U�����>��) .�_�Ye�O�u We appreciate the technical assistance provided by Yumiko Iwaki, Tokyo Metropolitan University. ���U���^���x�3bW��j1Xt0�ttp�����ᎎ�f �,e��&@��y��a`���X������|J�\.V��u@g;�Uh0p�iF��a ����� �'ý����* e0 5� 1 0 obj is available on our Permission Requests page. The catalytic activity of diethylenetriamine and dimethylethylenediamine with both copper(I) and copper(II) salts are compared, and possible mechanistic implications discussed. from the aromatic Finkelstein reaction, the following GC oven temperature programs was used: (i) 70 °C upon injection, (ii) hold at 70 °C for 2 min, (iii) increase the temperature to 250 °C at a rate of 45 °C per minute, (iv) hold at 250 °C for 5 min. with the reproduced material. Please enable JavaScript %���� You do not have JavaScript enabled. ? If you are the author of this article you still need to obtain permission to reproduce 5 Howick Place | London | SW1P 1WG. Reproduced material should be attributed as follows: If the material has been adapted instead of reproduced from the original RSC publication In contrast, no significant disproportionation was observed using dimethylethylenediamine as the ligand, and the solid-state structures of a copper(I) dimeric complex and a 2D polymeric network of copper(I) iodide tetramers are reported. This may take some time to load. article provided that the correct acknowledgement is given with the reproduced material. 2 0 obj Corresponding authors, a In contrast to earlier methods, the use of inert atmosphere conditions was not required to obtain high yields and purity. 177 0 obj <>/Filter/FlateDecode/ID[<566569DD26FC064FB54645BE18557428>]/Index[167 17]/Info 166 0 R/Length 64/Prev 624165/Root 168 0 R/Size 184/Type/XRef/W[1 2 1]>>stream to reproduce figures, diagrams etc. to access the full features of the site or access our, Department of Chemistry, Imperial College London, South Kensington, London, UK, Instructions for using Copyright Clearance Center page. There is occurrence of inversion of stereochemistry. the whole article in a third party publication with the exception of reproduction XX is the XXth reference in the list of references. Mechanism of organic reaction:  It is a simple one-step reaction and it involves SN2reaction.

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