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Synthesis 2021; 53(13): 2269-2276
DOI: 10.1055/a-1385-6119
DOI: 10.1055/a-1385-6119
paper
2-Pyridyl Sulfoxide Directed Pd(II)-Catalyzed C–H Olefination of Arenes with Molecular Oxygen as the Sole Oxidant
This work was supported by the Department of Science and Technology, Science and Engineering Research Board (DST-SERB, Grant Ref. No. EEQ/2017/000768) and the University Grants Commission [UGC, File No. 30-356/2017(BSR)]. M.Y., R.S.J., and B.S. thank the Council of Scientific and Industrial Research (CSIR), India and the Science and Engineering Research Board (SERB) for research fellowships. We thank the Department of Science and Technology, Fund for Improvement of S&T Infrastructure in Higher Educational Institutions [DST-FIST, Grant No. SR/FST/CSI-257/2014(C)] for a research grant to the Department of Chemistry, and also thank the Central University of Rajasthan for support.
Abstract
Pd(II)-catalyzed C–H olefination of aryl 2-pyridyl sulfoxides with unactivated and activated olefins has been demonstrated. We employed environmentally benign and inexpensive molecular oxygen as the sole oxidant. The versatile nature of the 2-pyridyl sulfoxide directing group has been proven by its transformation to the sulfone functionality. Deuterium scrambling experiments and intramolecular kinetic isotopic studies were carried out to gain insights into the reaction pathway.
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-1385-6119.
- Supporting Information
Publication History
Received: 28 January 2021
Accepted after revision: 08 February 2021
Accepted Manuscript online:
08 February 2021
Article published online:
23 February 2021
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19 The structures of regioisomers were assigned by analogy to compounds reported in the literature; see ref. 16b.
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20 Pd complex 6 has been synthesized in DCE and the structure unambiguously determined by X-ray analysis; see ref. 11b. Pd complex 6 synthesized in DCE and DMF showed identical peaks in the 1H NMR spectra (see the Supporting Information).
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21 One of the referees suggested the use of 1–2 equivalents of D2O instead of 10 equivalents of D2O as it is too much for the reaction. However, no deuterium incorporation was found even with 2 equivalents of D2O. Secondly, to avoid any interference of D2O in the palladation step, a similar reaction was performed without D2O and finally the reaction quenched with D2O to capture deuterated product. But, the 1H NMR data showed that no deuterated product was formed.