Synlett 2021; 32(04): 378-382
DOI: 10.1055/s-0040-1706681
cluster
Radicals – by Young Chinese Organic Chemists

Visible-Light-Driven Phosphonoalkylation of Alkenes

Yue-Ming Jiang
a  Urumqi Key Laboratory of Green Catalysis and Synthesis Technology, Key Laboratory of Energy Materials Chemistry, Ministry of Education; Key Laboratory of Advanced Functional Materials, Autonomous Region; Institute of Applied Chemistry, College of Chemistry, Xinjiang University, Urumqi 830046, Xinjiang, P. R. of China
b  Key Laboratory of Green Chemistry & Technology of Ministry of Education, College of Chemistry, Sichuan University, #29 Wangjiang Road, Chengdu 610064, P. R. of China
,
Jie Liu
b  Key Laboratory of Green Chemistry & Technology of Ministry of Education, College of Chemistry, Sichuan University, #29 Wangjiang Road, Chengdu 610064, P. R. of China
,
Qiang Fu
b  Key Laboratory of Green Chemistry & Technology of Ministry of Education, College of Chemistry, Sichuan University, #29 Wangjiang Road, Chengdu 610064, P. R. of China
c  School of Pharmacy, Southwest Medical University, Luzhou 646000, P. R. of China
,
Yu-Ming Yu
a  Urumqi Key Laboratory of Green Catalysis and Synthesis Technology, Key Laboratory of Energy Materials Chemistry, Ministry of Education; Key Laboratory of Advanced Functional Materials, Autonomous Region; Institute of Applied Chemistry, College of Chemistry, Xinjiang University, Urumqi 830046, Xinjiang, P. R. of China
,
Da-Gang Yu
b  Key Laboratory of Green Chemistry & Technology of Ministry of Education, College of Chemistry, Sichuan University, #29 Wangjiang Road, Chengdu 610064, P. R. of China
› Author Affiliations
We thank the National Natural Science Foundation of China (No. 21772129 and 21861038), the Fundamental Research Funds for the Central Universities, Scientific Research Program of the Higher Education Institution of Xinjiang (No. XJEDU2018Y015), and the Collaborative Fund of Luzhou Government and Southwest Medical University (2019LZXNYDJ28) for financial support.


Abstract

Phosphonylation of alkenes is important for the generation of valuable organophosphines. However, redox-neutral difunctionalization of alkenes with readily available H-P(O) compounds remains underdeveloped. Herein, we report the first visible-light-driven redox-neutral phosphonoalkylation of alkenes. A variety of organophosphorus-containing three-membered carbocyclic scaffolds are synthesized from alkene-bearing alkyl sulfonates with H-P(O) compounds. The transition-metal-free protocol displays good functional group tolerance, broad substrate scope, high yields, and mild reaction conditions.

Supporting Information



Publication History

Received: 30 October 2020

Accepted after revision: 23 December 2020

Publication Date:
12 February 2021 (online)

© 2021. Thieme. All rights reserved

Georg Thieme Verlag KG
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  • 14 Synthesis of 3aa: An oven-dried Schlenk tube (10 mL) containing a stirring bar was charged with 1a (0.2 mmol) and 4CzIPN (0.004 mmol, 3.2 mg, 2 mol%). Subsequently, the Schlenk tube was introduced in a glovebox, where it was charged with Cs2CO3 (0.3 mmol, 97.5 mg, 1.5 equiv) and HP(O)Ph2 (2a). The tube was taken out of the glovebox and connected to a vacuum line where it was evacuated and back-filled with N2 three times. DMF (2 mL) was then added under N2 flow and the reaction mixture was sealed in the tube and placed at a distance of 2–4 cm from a 30 W blue LED and stirred at room temperature (25 °C) for 1.5 h. The reaction was then quenched with H2O (1 mL), and the mixture was extracted with EtOAc and concentrated in vacuo. The residue was purified by silica gel flash chromatography (0.05% AcOH in petroleum ether/EtOAc = 1:1) to give the corresponding desired product 3aa (89.7 mg, 92%). 1H NMR (400 MHz, CDCl3): δ = 7.63–7.50 (m, 4 H), 7.46–7.39 (m, 4 H), 7.35 (m, 3 H), 7.28 (m, 4 H), 7.24–7.15 (m, 4 H), 2.74 (d, J = 10.2 Hz, 2 H), 1.16–1.05 (m, 2 H), 0.95 (q, J = 2.2 Hz, 2 H). 13C NMR (101 MHz, CDCl3): δ = 143.06 (d, J = 2.3 Hz), 141.05, 139.04, 133.55 (d, J = 97.3 Hz), 131.04 (d, J = 2.8 Hz), 130.53 (d, J = 9.2 Hz), 129.78, 128.63, 128.23 (d, J = 11.5 Hz), 126.98, 126.93, 126.62, 40.43 (d, J = 71.1 Hz), 20.51 (d, J = 4.6 Hz), 13.33 (d, J = 7.2 Hz). 31P NMR (162 MHz, CDCl3): δ = 28.78. HRMS: m/z [M + Na]+ calcd for C28H25OP: 431.1535; found: 431.1532.