Transition metal-free cross-dehydrogenative arylation of unactivated benzylic C-H bonds
The cross-dehydrogenative arylation of benzylic C-H bonds with arenes provides straightforward access to synthetically useful 1,1-diarylmethanes, from readily available starting materials. Current approaches suffer from limited substrate scope, requirement for large excesses of alkyl arene and/or no...
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| Published in: | Chemical communications (Cambridge, England) Vol. 56; no. 92; pp. 14479 - 14482 |
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| Main Authors: | , , , , , |
| Format: | Journal Article |
| Language: | English |
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Royal Soc Chemistry
19.11.2020
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| ISSN: | 1359-7345, 1364-548X, 1364-548X |
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| Abstract | The cross-dehydrogenative arylation of benzylic C-H bonds with arenes provides straightforward access to synthetically useful 1,1-diarylmethanes, from readily available starting materials. Current approaches suffer from limited substrate scope, requirement for large excesses of alkyl arene and/or non-trivial reaction set up. We report a transition metal-free cross-dehydrogenative arylation of benzylic C-H bonds using alkyl benzene derivatives and electron-rich arenes as coupling partners. The method proceeds through the in situ generation of a reactive benzyl fluoride intermediate which then reacts with the nucleophilic arene. The reaction tolerates a wide variety of functional groups including unprotected polar functionality and has been applied to the late-stage benzylation of several biologically relevant molecules. |
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| AbstractList | The cross-dehydrogenative arylation of benzylic C-H bonds with arenes provides straightforward access to synthetically useful 1,1-diarylmethanes, from readily available starting materials. Current approaches suffer from limited substrate scope, requirement for large excesses of alkyl arene and/or non-trivial reaction set up. We report a transition metal-free cross-dehydrogenative arylation of benzylic C-H bonds using alkyl benzene derivatives and electron-rich arenes as coupling partners. The method proceeds through the in situ generation of a reactive benzyl fluoride intermediate which then reacts with the nucleophilic arene. The reaction tolerates a wide variety of functional groups including unprotected polar functionality and has been applied to the late-stage benzylation of several biologically relevant molecules. The cross-dehydrogenative arylation of benzylic C-H bonds with arenes provides straightforward access to synthetically useful 1,1-diarylmethanes, from readily available starting materials. Current approaches suffer from limited substrate scope, requirement for large excesses of alkyl arene and/or non-trivial reaction set up. We report a transition metal-free cross-dehydrogenative arylation of benzylic C-H bonds using alkyl benzene derivatives and electron-rich arenes as coupling partners. The method proceeds through the in situ generation of a reactive benzyl fluoride intermediate which then reacts with the nucleophilic arene. The reaction tolerates a wide variety of functional groups including unprotected polar functionality and has been applied to the late-stage benzylation of several biologically relevant molecules.The cross-dehydrogenative arylation of benzylic C-H bonds with arenes provides straightforward access to synthetically useful 1,1-diarylmethanes, from readily available starting materials. Current approaches suffer from limited substrate scope, requirement for large excesses of alkyl arene and/or non-trivial reaction set up. We report a transition metal-free cross-dehydrogenative arylation of benzylic C-H bonds using alkyl benzene derivatives and electron-rich arenes as coupling partners. The method proceeds through the in situ generation of a reactive benzyl fluoride intermediate which then reacts with the nucleophilic arene. The reaction tolerates a wide variety of functional groups including unprotected polar functionality and has been applied to the late-stage benzylation of several biologically relevant molecules. |
| Author | Bentkowska, Katarzyna Larrosa, Igor Grainger, Rachel Spencer, Andrew R. A. Panigrahi, Adyasha Lepper, Thomas J. |
| Author_xml | – sequence: 1 givenname: Andrew R. A. surname: Spencer fullname: Spencer, Andrew R. A. organization: Univ Manchester, Sch Nat Sci, Dept Chem, Oxford Rd, Manchester M13 9PL, Lancs, England – sequence: 2 givenname: Rachel orcidid: 0000-0002-3944-0201 surname: Grainger fullname: Grainger, Rachel organization: Univ Manchester, Sch Nat Sci, Dept Chem, Oxford Rd, Manchester M13 9PL, Lancs, England – sequence: 3 givenname: Adyasha surname: Panigrahi fullname: Panigrahi, Adyasha organization: Univ Manchester, Sch Nat Sci, Dept Chem, Oxford Rd, Manchester M13 9PL, Lancs, England – sequence: 4 givenname: Thomas J. orcidid: 0000-0003-4255-7651 surname: Lepper fullname: Lepper, Thomas J. organization: Univ Manchester, Sch Nat Sci, Dept Chem, Oxford Rd, Manchester M13 9PL, Lancs, England – sequence: 5 givenname: Katarzyna surname: Bentkowska fullname: Bentkowska, Katarzyna organization: Univ Manchester, Sch Nat Sci, Dept Chem, Oxford Rd, Manchester M13 9PL, Lancs, England – sequence: 6 givenname: Igor orcidid: 0000-0002-5391-7424 surname: Larrosa fullname: Larrosa, Igor email: igor.larrosa@manchester.ac.uk organization: Univ Manchester, Sch Nat Sci, Dept Chem, Oxford Rd, Manchester M13 9PL, Lancs, England |
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| Keywords | F BONDS FUNCTIONALIZATION C(SP)-H BONDS ACTIVATION COUPLING REACTIONS LIGHT OXIDATIVE ARYLATION IRON FLUORINATION FLUORIDES |
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| Snippet | The cross-dehydrogenative arylation of benzylic C-H bonds with arenes provides straightforward access to synthetically useful 1,1-diarylmethanes, from readily... |
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| Title | Transition metal-free cross-dehydrogenative arylation of unactivated benzylic C-H bonds |
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