Conversion of 2-iodobiaryls into 2,2′-diiodobiaryls via oxidation-iodination sequences : a versatile route to ladder-type heterofluorenes
Even though 2,2′-diiodo- and 2,2′-dibromobiaryls represent accomplished precursors for heterofluorenes and other extended π-conjugated systems, their preparation still remains nontrivial when structural diversity of the biaryl backbone is required. Herein, we report a convenient method for the prepa...
| Main Authors: | , |
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| Other Authors: | |
| Format: | Journal Article |
| Language: | English |
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2015
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| Online Access: | https://hdl.handle.net/10356/105682 http://hdl.handle.net/10220/26055 http://dx.doi.org/10.1002/anie.201503134 |
| _version_ | 1826129481948987392 |
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| author | Wu, Bin Yoshikai, Naohiko |
| author2 | School of Physical and Mathematical Sciences |
| author_facet | School of Physical and Mathematical Sciences Wu, Bin Yoshikai, Naohiko |
| author_sort | Wu, Bin |
| collection | NTU |
| description | Even though 2,2′-diiodo- and 2,2′-dibromobiaryls represent accomplished precursors for heterofluorenes and other extended π-conjugated systems, their preparation still remains nontrivial when structural diversity of the biaryl backbone is required. Herein, we report a convenient method for the preparation of various 2,2′-diiodobiaryls from 2-iodobiaryls via cyclic diaryliodonium intermediates. An iodinative ring-opening of the diaryliodonium salts, mediated by a copper/diamine catalyst system, is able to afford the corresponding 2,2′-diiodobiaryls under mild conditions. The versatility of this two-step approach is demonstrated by the preparation of hitherto unexplored tetraiodoteraryls and their conversion into ladder-type π-conjugated systems. |
| first_indexed | 2024-10-01T07:41:19Z |
| format | Journal Article |
| id | ntu-10356/105682 |
| institution | Nanyang Technological University |
| language | English |
| last_indexed | 2024-10-01T07:41:19Z |
| publishDate | 2015 |
| record_format | dspace |
| spelling | ntu-10356/1056822019-12-06T21:55:45Z Conversion of 2-iodobiaryls into 2,2′-diiodobiaryls via oxidation-iodination sequences : a versatile route to ladder-type heterofluorenes Wu, Bin Yoshikai, Naohiko School of Physical and Mathematical Sciences DRNTU::Science::Chemistry::Organic chemistry::Heterocyclic compounds Even though 2,2′-diiodo- and 2,2′-dibromobiaryls represent accomplished precursors for heterofluorenes and other extended π-conjugated systems, their preparation still remains nontrivial when structural diversity of the biaryl backbone is required. Herein, we report a convenient method for the preparation of various 2,2′-diiodobiaryls from 2-iodobiaryls via cyclic diaryliodonium intermediates. An iodinative ring-opening of the diaryliodonium salts, mediated by a copper/diamine catalyst system, is able to afford the corresponding 2,2′-diiodobiaryls under mild conditions. The versatility of this two-step approach is demonstrated by the preparation of hitherto unexplored tetraiodoteraryls and their conversion into ladder-type π-conjugated systems. NRF (Natl Research Foundation, S’pore) 2015-06-24T07:56:44Z 2019-12-06T21:55:45Z 2015-06-24T07:56:44Z 2019-12-06T21:55:45Z 2015 2015 Journal Article Wu, B., & Yoshikai, N. (2015). Conversion of 2-iodobiaryls into 2,2′-diiodobiaryls via oxidation-iodination sequences : a versatile route to ladder-type heterofluorenes. Angewandte chemie International edition, 54(30), 8736-8739. 1433-7851 https://hdl.handle.net/10356/105682 http://hdl.handle.net/10220/26055 http://dx.doi.org/10.1002/anie.201503134 en Angewandte chemie International edition © 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim. |
| spellingShingle | DRNTU::Science::Chemistry::Organic chemistry::Heterocyclic compounds Wu, Bin Yoshikai, Naohiko Conversion of 2-iodobiaryls into 2,2′-diiodobiaryls via oxidation-iodination sequences : a versatile route to ladder-type heterofluorenes |
| title | Conversion of 2-iodobiaryls into 2,2′-diiodobiaryls via oxidation-iodination sequences : a versatile route to ladder-type heterofluorenes |
| title_full | Conversion of 2-iodobiaryls into 2,2′-diiodobiaryls via oxidation-iodination sequences : a versatile route to ladder-type heterofluorenes |
| title_fullStr | Conversion of 2-iodobiaryls into 2,2′-diiodobiaryls via oxidation-iodination sequences : a versatile route to ladder-type heterofluorenes |
| title_full_unstemmed | Conversion of 2-iodobiaryls into 2,2′-diiodobiaryls via oxidation-iodination sequences : a versatile route to ladder-type heterofluorenes |
| title_short | Conversion of 2-iodobiaryls into 2,2′-diiodobiaryls via oxidation-iodination sequences : a versatile route to ladder-type heterofluorenes |
| title_sort | conversion of 2 iodobiaryls into 2 2 diiodobiaryls via oxidation iodination sequences a versatile route to ladder type heterofluorenes |
| topic | DRNTU::Science::Chemistry::Organic chemistry::Heterocyclic compounds |
| url | https://hdl.handle.net/10356/105682 http://hdl.handle.net/10220/26055 http://dx.doi.org/10.1002/anie.201503134 |
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