doi: 10.1021/acs.orglett.7b01693.
Epub 2017 Jul 3.
Benzothiazole Sulfinate: A Sulfinic Acid Transfer Reagent under Oxidation-Free Conditions
Affiliations
- PMID: 28670905
- PMCID: PMC5863730
- DOI: 10.1021/acs.orglett.7b01693
Item in Clipboard
Benzothiazole Sulfinate: A Sulfinic Acid Transfer Reagent under Oxidation-Free Conditions
Org Lett.
.
Abstract
Sulfinic acids are commonly encountered intermediates found in natural product synthesis and medicinal chemistry. However, because of high reactivity, instability, and harsh reaction conditions, they are difficult to synthesize. Herein we have developed an oxidation-free method to produce sulfinic acids and sulfinate salts using 2-sulfinyl benzothiazole (BTS). We have also demonstrated the synthetic usefulness by developing one-pot syntheses of sulfones and sulfonamides.
Conflict of interest statement
The authors declare no competing financial interest.
Figures
Syntheses of Sulfinic Acids, Sulfones, and Sulfonamides
Similar articles
-
Generation of a cysteine sulfinic acid analog for incorporation in peptides using solid phase peptide synthesis.Bioorg Med Chem Lett. 2017 Jun 1;27(11):2410-2414. doi: 10.1016/j.bmcl.2017.04.019. Epub 2017 Apr 6. Bioorg Med Chem Lett. 2017. PMID: 28416133
-
One-pot synthesis of aryl sulfones from organometallic reagents and iodonium salts.J Org Chem. 2015 Mar 6;80(5):2582-600. doi: 10.1021/jo5027518. Epub 2015 Feb 17. J Org Chem. 2015. PMID: 25650485
-
Simple sulfinate synthesis enables C-H trifluoromethylcyclopropanation.Angew Chem Int Ed Engl. 2014 Sep 8;53(37):9851-5. doi: 10.1002/anie.201406622. Epub 2014 Aug 3. Angew Chem Int Ed Engl. 2014. PMID: 25088979 Free PMC article.
-
The Interaction of Hypotaurine and Other Sulfinates with Reactive Oxygen and Nitrogen Species: A Survey of Reaction Mechanisms.Adv Exp Med Biol. 2017;975 Pt 1:573-583. doi: 10.1007/978-94-024-1079-2_45. Adv Exp Med Biol. 2017. PMID: 28849483 Review.
-
Sulfinate derivatives: dual and versatile partners in organic synthesis.Org Biomol Chem. 2014 Dec 28;12(48):9743-59. doi: 10.1039/c4ob01727g. Org Biomol Chem. 2014. PMID: 25354469 Review.
Cited by
-
Synthetic and Mechanistic Studies of a Versatile Heteroaryl Thioether Directing Group for Pd(II) Catalysis.ACS Catal. 2019 Sep 6;9(9):7626-7640. doi: 10.1021/acscatal.9b01471. Epub 2019 Jul 2. ACS Catal. 2019. PMID: 32542117 Free PMC article.
-
Reductive sulfinylation by nucleophilic chain isomerization of sulfonylpyridinium.Nat Commun. 2025 Jan 3;16(1):377. doi: 10.1038/s41467-024-55786-7. Nat Commun. 2025. PMID: 39753559 Free PMC article.
-
Sulfur-Phenolate Exchange as a Mild, Fast, and High-Yielding Method toward the Synthesis of Sulfonamides.Org Lett. 2023 Feb 10;25(5):788-793. doi: 10.1021/acs.orglett.2c04292. Epub 2023 Jan 31. Org Lett. 2023. PMID: 36720015 Free PMC article.
-
Near-infrared light-triggered nano-prodrug for cancer gas therapy.J Nanobiotechnology. 2021 Dec 23;19(1):443. doi: 10.1186/s12951-021-01078-x. J Nanobiotechnology. 2021. PMID: 34949202 Free PMC article. Review.
-
Copper-Catalyzed Synthesis of Masked (Hetero)Aryl Sulfinates.Org Lett. 2024 Apr 12;26(14):2817-2820. doi: 10.1021/acs.orglett.3c03621. Epub 2024 Jan 8. Org Lett. 2024. PMID: 38189248 Free PMC article.
References
-
- Shavnya A, Coffey SB, Smith AC, Mascitti V. Org Lett. 2013;15:6226. - PubMed
-
- Shavnya A, Hesp KD, Mascitti V, Smith AC. Angew Chem, Int Ed. 2015;54:13571. - PubMed
-
- Shavnya A, Coffey SB, Hesp KD, Ross SC, Tsai AS. Org Lett. 2016;18:5848. - PubMed
-
- Gauthier DR, Yoshikawa N. Org Lett. 2016;18:5994. - PubMed
-
- Shyam PK, Jang HY. J Org Chem. 2017;82:1761. - PubMed
Publication types
MeSH terms
Substances
Grants and funding
LinkOut - more resources
Full Text Sources
Other Literature Sources
