Highly Regioselective Indoline Synthesis under Nickel/Photoredox Dual Catalysis
Nickel/photoredox catalysis is used to synthesize indolines in one step from iodoacetanilides and alkenes. Very high regioselectivity for 3-substituted indoline products is obtained for both aliphatic and styrenyl olefins. Mechanistic investigations indicate that oxidation to Ni(III) is necessary to...
| Main Authors: | , |
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| Other Authors: | |
| Format: | Article |
| Language: | en_US |
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American Chemical Society (ACS)
2017
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| Online Access: | http://hdl.handle.net/1721.1/110421 https://orcid.org/0000-0003-2315-6983 https://orcid.org/0000-0002-8601-7799 |
| _version_ | 1826202490942521344 |
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| author | Tasker, Sarah Zinnen Jamison, Timothy F |
| author2 | Massachusetts Institute of Technology. Department of Chemistry |
| author_facet | Massachusetts Institute of Technology. Department of Chemistry Tasker, Sarah Zinnen Jamison, Timothy F |
| author_sort | Tasker, Sarah Zinnen |
| collection | MIT |
| description | Nickel/photoredox catalysis is used to synthesize indolines in one step from iodoacetanilides and alkenes. Very high regioselectivity for 3-substituted indoline products is obtained for both aliphatic and styrenyl olefins. Mechanistic investigations indicate that oxidation to Ni(III) is necessary to perform the difficult C–N bond-forming reductive elimination, producing a Ni(I) complex, which in turn is reduced to Ni(0). This process serves to further demonstrate the utility of photoredox catalysts as controlled single electron transfer agents in multioxidation state nickel catalysis. |
| first_indexed | 2024-09-23T12:08:20Z |
| format | Article |
| id | mit-1721.1/110421 |
| institution | Massachusetts Institute of Technology |
| language | en_US |
| last_indexed | 2024-09-23T12:08:20Z |
| publishDate | 2017 |
| publisher | American Chemical Society (ACS) |
| record_format | dspace |
| spelling | mit-1721.1/1104212022-09-28T00:25:39Z Highly Regioselective Indoline Synthesis under Nickel/Photoredox Dual Catalysis Tasker, Sarah Zinnen Jamison, Timothy F Massachusetts Institute of Technology. Department of Chemistry Tasker, Sarah Zinnen Jamison, Timothy F Nickel/photoredox catalysis is used to synthesize indolines in one step from iodoacetanilides and alkenes. Very high regioselectivity for 3-substituted indoline products is obtained for both aliphatic and styrenyl olefins. Mechanistic investigations indicate that oxidation to Ni(III) is necessary to perform the difficult C–N bond-forming reductive elimination, producing a Ni(I) complex, which in turn is reduced to Ni(0). This process serves to further demonstrate the utility of photoredox catalysts as controlled single electron transfer agents in multioxidation state nickel catalysis. National Institute of General Medical Sciences (U.S.) (GM63755) 2017-07-03T15:09:16Z 2017-07-03T15:09:16Z 2015-08 2015-06 Article http://purl.org/eprint/type/JournalArticle 0002-7863 1520-5126 http://hdl.handle.net/1721.1/110421 Tasker, Sarah Z. and Jamison, Timothy F. “Highly Regioselective Indoline Synthesis Under Nickel/Photoredox Dual Catalysis.” Journal of the American Chemical Society 137, 30 (August 2015): 9531–9534 © 2015 American Chemical Society https://orcid.org/0000-0003-2315-6983 https://orcid.org/0000-0002-8601-7799 en_US http://dx.doi.org/10.1021/jacs.5b05597 Journal of the American Chemical Society Article is made available in accordance with the publisher's policy and may be subject to US copyright law. Please refer to the publisher's site for terms of use. application/pdf American Chemical Society (ACS) PMC |
| spellingShingle | Tasker, Sarah Zinnen Jamison, Timothy F Highly Regioselective Indoline Synthesis under Nickel/Photoredox Dual Catalysis |
| title | Highly Regioselective Indoline Synthesis under Nickel/Photoredox Dual Catalysis |
| title_full | Highly Regioselective Indoline Synthesis under Nickel/Photoredox Dual Catalysis |
| title_fullStr | Highly Regioselective Indoline Synthesis under Nickel/Photoredox Dual Catalysis |
| title_full_unstemmed | Highly Regioselective Indoline Synthesis under Nickel/Photoredox Dual Catalysis |
| title_short | Highly Regioselective Indoline Synthesis under Nickel/Photoredox Dual Catalysis |
| title_sort | highly regioselective indoline synthesis under nickel photoredox dual catalysis |
| url | http://hdl.handle.net/1721.1/110421 https://orcid.org/0000-0003-2315-6983 https://orcid.org/0000-0002-8601-7799 |
| work_keys_str_mv | AT taskersarahzinnen highlyregioselectiveindolinesynthesisundernickelphotoredoxdualcatalysis AT jamisontimothyf highlyregioselectiveindolinesynthesisundernickelphotoredoxdualcatalysis |