Straightforward synthesis of 2- and 2,8-substituted tetracenes
A simple regiospecific route to otherwise problematic substituted tetracenes is described. The diverse cores (E)- 1,2-Ar1CH2(HOCH2)C=C(CH2OH)I (Ar1 = Ph, 4-MePh, 4-MeOPh, 4-FPh) and (E)-1,2-I(HOCH2)C=C(CH2OH)I, accessed from ultra-low cost HOCH2C≡CCH2OH at multi-gram scales, allow the synthesis of d...
| Main Authors: | , , , , , , , , , |
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| Format: | Article |
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Wiley-VCH Verlag
2017
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| Online Access: | https://eprints.nottingham.ac.uk/42527/ |
| _version_ | 1848796507545796608 |
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| author | Woodward, Simon Ackermann, Miriam Ahirwar, Saurabh Burroughs, Laurence Robert Garrett, Mary Ritchie, John Shine, Jonathan Tyril, Bjork Simpson, Kevin Woodward, Peter |
| author_facet | Woodward, Simon Ackermann, Miriam Ahirwar, Saurabh Burroughs, Laurence Robert Garrett, Mary Ritchie, John Shine, Jonathan Tyril, Bjork Simpson, Kevin Woodward, Peter |
| author_sort | Woodward, Simon |
| building | Nottingham Research Data Repository |
| collection | Online Access |
| description | A simple regiospecific route to otherwise problematic substituted tetracenes is described. The diverse cores (E)- 1,2-Ar1CH2(HOCH2)C=C(CH2OH)I (Ar1 = Ph, 4-MePh, 4-MeOPh, 4-FPh) and (E)-1,2-I(HOCH2)C=C(CH2OH)I, accessed from ultra-low cost HOCH2C≡CCH2OH at multi-gram scales, allow the synthesis of diol libraries (E)-1,2- Ar1CH2(HOCH2)C=C(CH2OH)CH2Ar2 (Ar2 = Ph, 4-MePh, 4-iPrPh, 4-MeOPh, 4-FPh, 4-BrPh, 4-biphenyl, 4-styryl; 14 examples) by efficient Negishi coupling. Copper-catalysed aerobic oxidation cleanly provides dialdehydes (E)-1,2- Ar1CH2(CHO)C=C(CHO)CH2Ar2 which in many cases undergo titanium(IV) chloride induced double Bradsher closure providing a convenient method for the synthesis of regiochemically and analytically pure tetracenes (12 examples). The sequence is typically chromatography-free, scalable, efficient and technically simple to carry out. |
| first_indexed | 2025-11-14T19:49:05Z |
| format | Article |
| id | nottingham-42527 |
| institution | University of Nottingham Malaysia Campus |
| institution_category | Local University |
| last_indexed | 2025-11-14T19:49:05Z |
| publishDate | 2017 |
| publisher | Wiley-VCH Verlag |
| recordtype | eprints |
| repository_type | Digital Repository |
| spelling | nottingham-425272020-05-04T18:46:23Z https://eprints.nottingham.ac.uk/42527/ Straightforward synthesis of 2- and 2,8-substituted tetracenes Woodward, Simon Ackermann, Miriam Ahirwar, Saurabh Burroughs, Laurence Robert Garrett, Mary Ritchie, John Shine, Jonathan Tyril, Bjork Simpson, Kevin Woodward, Peter A simple regiospecific route to otherwise problematic substituted tetracenes is described. The diverse cores (E)- 1,2-Ar1CH2(HOCH2)C=C(CH2OH)I (Ar1 = Ph, 4-MePh, 4-MeOPh, 4-FPh) and (E)-1,2-I(HOCH2)C=C(CH2OH)I, accessed from ultra-low cost HOCH2C≡CCH2OH at multi-gram scales, allow the synthesis of diol libraries (E)-1,2- Ar1CH2(HOCH2)C=C(CH2OH)CH2Ar2 (Ar2 = Ph, 4-MePh, 4-iPrPh, 4-MeOPh, 4-FPh, 4-BrPh, 4-biphenyl, 4-styryl; 14 examples) by efficient Negishi coupling. Copper-catalysed aerobic oxidation cleanly provides dialdehydes (E)-1,2- Ar1CH2(CHO)C=C(CHO)CH2Ar2 which in many cases undergo titanium(IV) chloride induced double Bradsher closure providing a convenient method for the synthesis of regiochemically and analytically pure tetracenes (12 examples). The sequence is typically chromatography-free, scalable, efficient and technically simple to carry out. Wiley-VCH Verlag 2017-05-19 Article PeerReviewed Woodward, Simon, Ackermann, Miriam, Ahirwar, Saurabh, Burroughs, Laurence, Robert Garrett, Mary, Ritchie, John, Shine, Jonathan, Tyril, Bjork, Simpson, Kevin and Woodward, Peter (2017) Straightforward synthesis of 2- and 2,8-substituted tetracenes. Chemistry - A European Journal . ISSN 1521-3765 acenes; aldehydes; arenes; aromaticity; Bradsher cyclization; C−C coupling http://onlinelibrary.wiley.com/doi/10.1002/chem.201701170/abstract doi:10.1002/chem.201701170 doi:10.1002/chem.201701170 |
| spellingShingle | acenes; aldehydes; arenes; aromaticity; Bradsher cyclization; C−C coupling Woodward, Simon Ackermann, Miriam Ahirwar, Saurabh Burroughs, Laurence Robert Garrett, Mary Ritchie, John Shine, Jonathan Tyril, Bjork Simpson, Kevin Woodward, Peter Straightforward synthesis of 2- and 2,8-substituted tetracenes |
| title | Straightforward synthesis of 2- and 2,8-substituted tetracenes |
| title_full | Straightforward synthesis of 2- and 2,8-substituted tetracenes |
| title_fullStr | Straightforward synthesis of 2- and 2,8-substituted tetracenes |
| title_full_unstemmed | Straightforward synthesis of 2- and 2,8-substituted tetracenes |
| title_short | Straightforward synthesis of 2- and 2,8-substituted tetracenes |
| title_sort | straightforward synthesis of 2- and 2,8-substituted tetracenes |
| topic | acenes; aldehydes; arenes; aromaticity; Bradsher cyclization; C−C coupling |
| url | https://eprints.nottingham.ac.uk/42527/ https://eprints.nottingham.ac.uk/42527/ https://eprints.nottingham.ac.uk/42527/ |