Ti(O-i-Pr)4/Me3SiCl/Mg-Mediated Reductive Cleavage of Sulfonamides and Sulfonates to Amines and Alcohols
A low-valent titanium generated in situ from Ti(O-i-Pr)4, Me3SiCl, and Mg powder in THF reacted with aryl- and alkyl-sulfonamides of aryl and alkyl amines in a reductive N–S/S–O/S–C bond cleaving pathway to provide the corresponding amines and hydrocarbons (and thiols) derived from the sulfonyl moie...
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| Veröffentlicht in: | Organic letters 2011-05, Vol.13 (10), p.2626-2629 |
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| container_end_page | 2629 |
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| container_issue | 10 |
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| container_title | Organic letters |
| container_volume | 13 |
| creator | Shohji, Noriaki Kawaji, Tsuyoshi Okamoto, Sentaro |
| description | A low-valent titanium generated in situ from Ti(O-i-Pr)4, Me3SiCl, and Mg powder in THF reacted with aryl- and alkyl-sulfonamides of aryl and alkyl amines in a reductive N–S/S–O/S–C bond cleaving pathway to provide the corresponding amines and hydrocarbons (and thiols) derived from the sulfonyl moiety. The reagent could also cleave sulfonates to the corresponding alcohols. |
| doi_str_mv | 10.1021/ol200740r |
| format | Article |
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The reagent could also cleave sulfonates to the corresponding alcohols.</description><subject>Alcohols - chemistry</subject><subject>Amines - chemical synthesis</subject><subject>Amines - chemistry</subject><subject>Catalysis</subject><subject>Combinatorial Chemistry Techniques</subject><subject>Magnesium - chemistry</subject><subject>Molecular Structure</subject><subject>Sulfhydryl Compounds - chemical synthesis</subject><subject>Sulfhydryl Compounds - chemistry</subject><subject>Sulfonamides - chemistry</subject><subject>Titanium - chemistry</subject><issn>1523-7060</issn><issn>1523-7052</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2011</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNo9kMlOwzAQQC0EoqVw4AdQLgg4hNpO7KTHKmKTWhXRco4m9rR15cQlTirx9wR1Oc32NJp5hNwy-swoZ0NnOaVJTOsz0meCR2FCBT8_5ZL2yJX3G0pZ1xldkh5nglHJZJ-sF-ZxFprws36Kh1OM5iazw-kqnKI20KAOvlC3qjE7DDKLsIMVBm4ZzFu7dBWURqMPoNLHRtOVjQvGpakOg7FVbu2svyYXS7Aebw5xQL5fXxbZeziZvX1k40kInLMmLBKGGiOFkMZKUhErABh1PwgRQYyAAnmhkBVaYjpKUhlpKaiKElBFwmkcDcjDfu-2dj8t-iYvjVdoLVToWp-nUnYOYjHqyLsD2RYl6nxbmxLq3_wopwPu9wAon29cW1fd4Tmj-b_0_CQ9-gOfWnCE</recordid><startdate>20110520</startdate><enddate>20110520</enddate><creator>Shohji, Noriaki</creator><creator>Kawaji, Tsuyoshi</creator><creator>Okamoto, Sentaro</creator><general>American Chemical Society</general><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>7X8</scope></search><sort><creationdate>20110520</creationdate><title>Ti(O-i-Pr)4/Me3SiCl/Mg-Mediated Reductive Cleavage of Sulfonamides and Sulfonates to Amines and Alcohols</title><author>Shohji, Noriaki ; Kawaji, Tsuyoshi ; Okamoto, Sentaro</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a221t-b71ede3cea84c6054caaa9706553a4eae5e2bce1bd6e897863d650c37acb72043</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2011</creationdate><topic>Alcohols - chemistry</topic><topic>Amines - chemical synthesis</topic><topic>Amines - chemistry</topic><topic>Catalysis</topic><topic>Combinatorial Chemistry Techniques</topic><topic>Magnesium - chemistry</topic><topic>Molecular Structure</topic><topic>Sulfhydryl Compounds - chemical synthesis</topic><topic>Sulfhydryl Compounds - chemistry</topic><topic>Sulfonamides - chemistry</topic><topic>Titanium - chemistry</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Shohji, Noriaki</creatorcontrib><creatorcontrib>Kawaji, Tsuyoshi</creatorcontrib><creatorcontrib>Okamoto, Sentaro</creatorcontrib><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>MEDLINE - Academic</collection><jtitle>Organic letters</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Shohji, Noriaki</au><au>Kawaji, Tsuyoshi</au><au>Okamoto, Sentaro</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Ti(O-i-Pr)4/Me3SiCl/Mg-Mediated Reductive Cleavage of Sulfonamides and Sulfonates to Amines and Alcohols</atitle><jtitle>Organic letters</jtitle><addtitle>Org. 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| fulltext | fulltext |
| identifier | ISSN: 1523-7060 |
| ispartof | Organic letters, 2011-05, Vol.13 (10), p.2626-2629 |
| issn | 1523-7060 1523-7052 |
| language | eng |
| recordid | cdi_proquest_miscellaneous_866529459 |
| source | MEDLINE; American Chemical Society (ACS) Journals |
| subjects | Alcohols - chemistry Amines - chemical synthesis Amines - chemistry Catalysis Combinatorial Chemistry Techniques Magnesium - chemistry Molecular Structure Sulfhydryl Compounds - chemical synthesis Sulfhydryl Compounds - chemistry Sulfonamides - chemistry Titanium - chemistry |
| title | Ti(O-i-Pr)4/Me3SiCl/Mg-Mediated Reductive Cleavage of Sulfonamides and Sulfonates to Amines and Alcohols |
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