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Z. Huang et al.
Letter
Synlett
the reaction of cyclohexene under standard conditions, the
yield of the addition product 3q fell to 23%, confirming that
our hypothesis was correct.
(4) (a) Sobhani, S.; Rezazadeh, S. Synlett 2010, 1485. (b) Ali, T. E.
Heteroat. Chem. 2013, 24, 426. (c) Green, K. Tetrahedron Lett.
1989, 30, 4807.
(5) (a) Salin, A. V.; I’lin, A. V.; Faskhutdinov, R. I.; Galkin, V. I.;
Islamov, D. R.; Kataeva, O. N. Tetrahedron Lett. 2018, 59, 1630.
(b) Huang, T.-Z.; Chen, T.; Saga, Y.; Han, L.-B. Tetrahedron 2017,
73, 7085. (c) Saga, Y.; Han, D.; Kawaguchi, S.-i.; Ogawa, A.; Han,
L.-B. Tetrahedron Lett. 2015, 56, 5303. (d) Salin, A. V.; Il’in, A. V.;
Shamsutdinova, F. G. Curr. Org. Synth. 2016, 13, 132.
(6) (a) Han, L.-B.; Zhao, C.-Q. J. Org. Chem. 2005, 70, 10121.
(b) Farnham, W. B.; Murray, R. K.; Mislow, K. J. Chem. Soc. D
1971, 146. (c) Semenzin, D.; Etemad-Moghadam, G.; Albouy, D.;
Diallo, O.; Koenig, M. J. Org. Chem. 1997, 62, 2414. (d) Hirai, T.;
Han, L.-B. Org. Lett. 2007, 9, 53.
O
O
BHT (2 equiv)
P
H
Bu
3a 89%
+
Ph
Ph
Ph
Ph
Ph
Ph
O
standard conditions
O
no base
P
H
3q 37%
3q 23%
+
+
100 °C, 12 h, N2
O
BHT (2 equiv)
P
H
standard conditions
Scheme 3 Control experiment
(7) (a) Lenker, H. K.; Richard, M. E.; Reese, K. P.; Carter, A. F.;
Zawisky, J. D.; Winter, E. F.; Bergeron, T. W.; Guydon, K. S.;
Stockland, R. A. Jr. J. Org. Chem. 2012, 77, 1378. (b) Stockland, R.
A.; Taylor, R. I.; Thompson, L. E.; Patel, P. B. Org. Lett. 2005, 7,
851.
(8) (a) Rulev, A. Y.; Larina, L. I.; Voronkov, M. G. Tetrahedron Lett.
2000, 41, 10211. (b) Keglevich, G.; Sipos, M.; Takács, D.; Greiner,
I. Heteroat. Chem. 2007, 18, 226.
In conclusion, we have developed a weak-base-promot-
ed hydrophosphonylation reaction of alkenes with disubsti-
tuted phosphine oxides under mild conditions.15 A series of
electron-deficient olefins with terminal nonactivated
alkene groups, as well as chalcones, are suitable substrates
for this transformation, giving moderate to good yields.
(9) (a) Miller, R. C.; Bradley, J. S.; Hamilton, L. A. J. Am. Chem. Soc.
1956, 78, 5299. (b) Bunlaksananusorn, T.; Knochel, P. Tetrahe-
dron Lett. 2002, 43, 5817.
(10) Wen, S.; Li, P.; Wu, H.; Yu, F.; Liang, X.; Ye, J. Chem. Commun.
2010, 46, 4806.
(11) Wang, J.-P.; Nie, S.-Z.; Zhou, Z.-Y.; Ye, J.-J.; Wen, J.-H.; Zhao, C.-Q.
J. Org. Chem. 2016, 81, 7644.
(12) (a) Lachia, M.; Iriart, S.; Baalouch, M.; De Mesmaeker, A.;
Beaudegnies, R. Tetrahedron Lett. 2011, 52, 3219. (b) Jiang, Z.;
Zhang, Y.; Ye, W.; Tan, C.-H. Tetrahedron Lett. 2007, 48, 51.
(c) Zhu, X.-Y.; Chen, J.-R.; Lu, L.-Q.; Xiao, W.-J. Tetrahedron 2012,
68, 6032.
(13) (a) Zhao, D.; Wang, L.; Yang, D.; Zhang, Y.; Wang, R. Chem. Asian
J. 2012, 7, 881. (b) Zhao, E.; Mao, L.; Yang, D.; Wang, R. Chem.
Commun. 2012, 48, 889. (c) Zhao, E.; Mao, L.; Yang, D.; Wang, R.
J. Org. Chem. 2010, 75, 6756.
(14) (a) Huang, L.; Gong, J.; Zhu, Z.; Wang, Y.; Guo, S.; Cai, H. Org.
Lett. 2017, 19, 2242. (b) Gong, J.; Huang, L.; Deng, Q.; Jie, K.;
Wang, Y.; Guo, S.; Cai, H. Org. Chem. Front. 2017, 4, 1781.
(c) Wang, Y.; Yang, Y.; Jie, K.; Huang, L.; Guo, S.; Cai, H. Chem-
CatChem 2018, 10, 716. (d) Guo, S.; Jie, K.; Zhang, Z.; Fu, Z.; Cai,
H. Eur. J. Org. Chem. 2019, 1808. (e) Guo, S.; Jie, K.; Huang, L.;
Zhang, Z.; Wang, Y.; Fu, Z.; Cai, H. Synlett 2019, 30, 1090.
(f) Huang, L.; Zhang, Z.; Jie, K.; Wang, Y.; Fu, Z.; Guo, S.; Cai, H.
Org. Chem. Front. 2018, 5, 3548. (g) Wang, Y.; Yang, Y.; Huang, L.;
Jie, K.; Guo, S.; Cai, H. Youji Huaxue 2017, 37, 3220.
(15) Butyl 3-(Diphenylphosphoryl)propanoate (3a); Typical Pro-
cedure
Funding Information
We thank the National Natural Science Foundation of China
(21861024, 21571094, 21571094) for financial support.
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References and Notes
(1) (a) Babine, R. E.; Bender, S. L. Chem. Rev. 1997, 97, 1359.
(b) Baumgartner, T.; Réau, R. Chem. Rev. 2006, 106, 4681; corri-
gendum: Chem. Rev. 2007, 107, 303. (c) Boëdec, A.; Sicard, H.;
Dessolin, J.; Herbette, G.; Ingoure, S.; Raymond, C.; Belmant, C.;
Kraus, J.-L. J. Med. Chem. 2008, 51, 1747. (d) Yang, Y.; Coward, J.
K. J. Org. Chem. 2007, 72, 5748. (e) Tang, W.; Zhang, X. Chem.
Rev. 2003, 103, 3029. (f) Feng, Y.; Coward, J. K. J. Med. Chem.
2006, 49, 770.
(2) (a) Enders, D.; Saint-Dizier, A.; Lannou, M.-I.; Lenzen, A. Eur. J.
Org. Chem. 2006, 29. (b) Rulev, A. Y. RSC Adv. 2014, 4, 26002.
(c) Greenberg, Z. S.; Stephan, D. W. Chem. Soc. Rev. 2008, 37, 1482.
(d) Coudray, L.; Montchamp, J.-L. Eur. J. Org. Chem. 2008, 3601.
(3) (a) Woo, W.-J.; Kobayashi, S. Green Chem. 2013, 15, 1844. (b) Li,
Z.; Fan, F.; Zhang, Z.; Xiao, Y.; Liu, D.; Liu, Z.-Q. RSC Adv. 2015, 5,
27853. (c) Tayama, H.; Nakano, A.; Iwahama, T.; Sakaguchi, S.;
Ishii, Y. J. Org. Chem. 2004, 69, 5494. (d) Bravo-Altamirano, K.;
Coudray, L.; Deal, E. L.; Montchamp, J.-L. Org. Biomol. Chem.
2010, 8, 5541. (e) Duraud, A.; Toffano, M.; Fiaud, J.-C. Eur. J. Org.
Chem. 2009, 4400. (f) Ajellal, N.; Thomas, C. M.; Carpentier, J.-F.
Adv. Synth. Catal. 2006, 348, 1093. (g) Reichwein, J. F.; Patel, M.
C.; Pagenkopf, B. L. Org. Lett. 2001, 3, 4303. (h) Leyva-Pérez, A.;
Vidal-Moya, J. A.; Cabrero-Antonino, J. R.; Al-Deyab, S. S.; Al-
Resayes, S. I.; Corma, A. J. Organomet. Chem. 2010, 696, 362.
A mixture of 1a (0.4 mmol), 2a (0.8 mmol), and K2CO3 (0.8
mmol) in DCE (2 mL) was heated at 100 °C under N2 for 4 h. The
mixture was then extracted with DCE (3 × 5 mL) and the com-
bined organic phase was dried (Na2SO4), filtered, and concen-
trated under reduced pressure. The residue was purified by TLC
[silica gel, PE–EtOAc (3:1)] to give a colorless liquid; yield: 132
mg (95%).
1H NMR (400 MHz, CDCl3): = 7.68 (dd, J = 10.9, 7.6 Hz, 4 H),
7.43 (dd, J = 21.7, 6.4 Hz, 6 H), 3.96 (t, J = 6.6 Hz, 2 H), 2.55 (s, 4
H), 1.48 (pent, J = 6.8 Hz, 2 H), 1.25 (hept, J = 7.3 Hz, 2 H), 0.82 (t,
J = 7.4 Hz, 3 H). HRMS (ESI): m/z [M + H]+ calcd for C19H24O3P:
331.1458; found: 331.1467.
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