Journal
ACS CATALYSIS
Volume 7, Issue 2, Pages 1108-1112Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acscatal.6b03434
Keywords
sulfone; Suzuki-Miyaura cross-coupling; C-SO2 activation; palladium catalysis; iterative coupling
Categories
Funding
- KAKENHI from JSPS [26810056]
- JSPS
- NU
- Natural Sciences and Engineering Research Council of Canada (NSERC)
- Canada Foundation for Innovation (CFI)
- Queen's University
- Grants-in-Aid for Scientific Research [26810056, 16F16749, 16K13962, 26288023] Funding Source: KAKEN
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The development of fluorinated sulfone derivatives as versatile electrophiles for Suzuki Miyaura cross-coupling reactions is described. Introducing electron-withdrawing groups on the aryl ring of the sulfone facilitates the Pd-catalyzed activation of C-SO2 bonds. Cross-coupling reactions with fluorinated sulfone electrophiles are reported, leading to a variety of multiply arylated products in good yields. The reactivity of this unusual electrophile is benchmarked versus common electrophiles and its use in iterative cross-couplings for concise synthesis of biologically active molecules is described.
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