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Synlett 2022; 33(17): 1745-1750
DOI: 10.1055/a-1915-8309
DOI: 10.1055/a-1915-8309
letter
HFIP-Induced Allylation Reaction of Tertiary Allylic Alcohols with Thiols or Sulfonyl Hydrazines to Access Allylic Organosulfurs
The project is supported by the National Natural Science Foundation of China (22171177, 51973107), STU Scientific Research Foundation for Talents (NTF18003), the Guangdong Province Universities and Colleges Pearl River Scholar Funded Scheme 2019 (GDUPS2019), the Chemistry and Chemical Engineering Guangdong Laboratory (1922003), and the Guangdong Major Project of Basic and Applied Basic Research (2019B030302009).
Abstract
A simple and transition-metal-free HFIP-induced allylation reaction of tertiary allylic alcohols with thiols or sulfonyl hydrazine derivatives was reported for the efficient and highly selective synthesis of allylic sulfides and allylic sulfones. Herein, HFIP played a vital role in not only activating the allylic alcohol, but also stabilizing the allylic cation intermediate to accelerate the subsequent transformations.
Supporting Information
- Supporting information for this
article is available online at
https://doi.org/10.1055/a-1915-8309.
- Supporting Information
- CIF File
Publication History
Received: 18 July 2022
Accepted after revision: 02 August 2022
Accepted Manuscript online:
02 August 2022
Article published online:
21 September 2022
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- 17 Cyclohexyl(3,3-diphenylallyl)sulfane (c1) – Typical Procedure1,1-Diphenylprop-2-en-1-ol (60.0 mg, 0.3 mmol), cyclohexyl mercaptan (50.0 mg, 0.45 mmol), HFIP (500.0 mg, 3.0 mmol), and magnetic stirring bar was added in a 10.0 mL flask. The reaction mixture stirred at the room temperature for 10 h, after which time TLC indicated complete consumption of starting substrate 1,1-diphenylprop-2-en-1-ol. The solvent was concentrated and purified by flash chromatography on silica gel (Hex/EtOAc = 60:1) to give the desired product c1 as a white solid (78.6 mg, 85% yield). 1H NMR (400 MHz, CDCl3): δ = 7.39–7.31 (m, 3 H), 7.30–7.23 (m, 5 H), 7.21–7.19 (m, 2 H), 6.15 (t, J = 7.8 Hz, 1 H), 3.25 (d, J = 7.8 Hz, 2 H), 2.61–2.55 (m, 1 H), 1.80–1.57 (m, 5 H), 1.23–1.17 (m, 5 H). 13C NMR (100 MHz, CDCl3): δ = 143.1, 142.1, 139.2, 130.0, 128.2, 128.1, 127.5, 127.4, 127.3, 125.9, 42.8, 33.6, 29.4, 26.2, 25.8. HRMS (ESI): m/z calcd for C21H25S [M + H+]