Communication
ChemComm
7 (a) T. Hirao, T. Masunaga, Y. Ohshiro and T. Agawa, Synthesis, 1981,
56–57; (b) M. Kalek, A. Ziadi and J. Stawinski, Org. Lett., 2008, 10,
4637–4640; (c) D. Gelman, L. Jiang and S. L. Buchwald, Org. Lett.,
2003, 5, 2315–2318; (d) A. J. Bloomfield and S. B. Herzon, Org. Lett.,
2012, 14, 4370–4373; (e) E. L. Deal, C. Petit and J.-L. Montchamp,
Org. Lett., 2011, 13, 3270–3273; ( f ) X. Zhang, H. Liu, X. Hu, G. Tang,
J. Zhu and Y. Zhao, Org. Lett., 2011, 13, 3478–3481; (g) C. Huang,
X. Tang, H. Fu, Y. Jiang and Y. Zhao, J. Org. Chem., 2006, 71,
5020–5022; (h) J.-L. Montchamp and Y. R. Dumond, J. Am. Chem.
Soc., 2001, 123, 510–511; (i) Y.-L. Zhao, G.-J. Wu, Y. Li, L.-X. Gao and
F.-S. Han, Chem. – Eur. J., 2012, 18, 9622–9627; ( j) K. Xu, F. Yang,
G. Zhang and Y. Wu, Green Chem., 2013, 15, 1055–1060.
8 (a) G. Yang, C. Shen, L. Zhang and W. Zhang, Tetrahedron Lett., 2011,
52, 5032–5035; (b) J. Yang, J. Xiao, T. Chen and L.-B. Han, J. Org.
Chem., 2016, 81, 3911–3916; (c) W. C. Fu, C. M. So and F. Y. Kwong,
Org. Lett., 2015, 17, 5906–5909; (d) Y.-L. Zhao, G.-J. Wu and
F.-S. Han, Chem. Commun., 2012, 48, 5868–5870; (e) J. Yang,
T. Chen and L.-B. Han, J. Am. Chem. Soc., 2015, 137, 1782–1785;
( f ) M. Kalek, M. Jezowska and J. Stawinski, Adv. Synth. Catal., 2009,
351, 3207–3216.
C–O cleavage. This aromatic Arbuzov-type reaction proceeded at
room temperature with broad substrate scope in moderate to
good yields in the absence of transition-metal and external
photosensitizer. In addition, the method has been successfully
employed in the late-stage phosphonation of biologically active
phenolic compounds. The mechanistic investigations show that
the reaction involves SET process, radical formation and Arbuzov-
type rearrangement. This method provides a promising pathway
for green synthesis of arylphosphorous compounds without
external transition-metal catalysts or photosensitizer under mild
conditions. The chemical transformations of other aryl electro-
philes are underway in our laboratory.
We thank the NSFC (21971093), the International Joint
Research Centre for Green Catalysis and Synthesis (grant no.
2016B01017 and 18JR4RA003), the 111 project and Post-doctoral
Foundation Project of Shenzhen Polytechnic (6021330006K) for
support of our research. We also thank the Canada Research
Chair (Tier I) foundation, the E. B. Eddy Endowment Fund, the
CFI, NSERC, and FQRNT to C.-J. Li.
¨
9 R. S. Shaikh, S. J. S. Du¨sel and B. Konig, ACS Catal., 2016, 6,
8410–8414.
10 L.-L. Liao, Y.-Y. Gui, X.-B. Zhang, G. Shen, H.-D. Liu, W.-J. Zhou, J. Li
and D.-G. Yu, Org. Lett., 2017, 19, 3735–3738.
11 (a) M. Fagnoni and A. Albini, Acc. Chem. Res., 2005, 38, 713–721;
(b) W. Liu, J. Li, C.-Y. Huang and C.-J. Li, Angew. Chem., Int. Ed.,
2020, 59, 1786–1796; (c) Y. Lang, C.-J. Li and H. Zeng, Org. Chem.
Front., 2021, 8, 3594–3613; (d) D. Cao, P. Pan, C.-J. Li and H. Zeng,
Green Synth. Catal., 2021, DOI: 10.1016/j.gresc.2021.04.006;
(e) Y. Lang, X. Peng, C.-J. Li and H. Zeng, Green Chem., 2020, 22,
6323–6327; ( f ) L. Li, W. Liu, X. Mu, Z. Mi and C.-J. Li, Nat. Protoc.,
2016, 11, 1948–1954; (g) H. Zeng, Q. Dou and C.-J. Li, Org. Lett.,
2019, 21, 1301–1305; (h) D. Cao, C. Yan, P. Zhou, H. Zeng and
C.-J. Li, Chem. Commun., 2019, 55, 767–770; (i) L. Li, W. Liu, H. Zeng,
X. Mu, G. Cosa, Z. Mi and C.-J. Li, J. Am. Chem. Soc., 2015, 137,
8328–8331; ( j) V. Dichiarante, M. Fagnoni and A. Albini, Chem.
Commun., 2006, 3001–3003; (k) A. M. Mfuh, J. D. Doyle, B. Chhetri,
H. D. Arman and O. V. Larionov, J. Am. Chem. Soc., 2016, 138,
2985–2988; (l) M. Fagnoni, M. Mella and A. Albini, Org. Lett., 1999, 1,
1299–1301; (m) M. De Carolis, S. Protti, M. Fagnoni and A. Albini,
Angew. Chem., Int. Ed., 2005, 44, 1232–1236; (n) V. Dichiarante,
M. Fagnoni and A. Albini, Angew. Chem., Int. Ed., 2007, 46,
6495–6498; (o) S. Protti, M. Fagnoni and A. Albini, Angew. Chem.,
Int. Ed., 2005, 44, 5675–5678; (p) D. Cao, Z. Chen, L. Lv, H. Zeng,
Y. Peng and C.-J. Li, iScience, 2020, 23, 101419; (q) Y. Kim and
C.-J. Li, Green Synth. Catal., 2020, 1, 1–11; (r) Q. Dou, Y. Lang,
H. Zeng and C.-J. Li, Fundam. Res., 2021, DOI: 10.1016/
j.fmre.2021.06.018.
Conflicts of interest
There are no conflicts to declare.
Notes and references
1 (a) J. Zakzeski, P. C. A. Bruijnincx, A. L. Jongerius and B. M.
Weckhuysen, Chem. Rev., 2010, 110, 3552–3599; (b) W. Schutyser,
T. Renders, S. Van den Bosch, S. F. Koelewijn, G. T. Beckham and
B. F. Sels, Chem. Soc. Rev., 2018, 47, 852–908.
´
2 (a) H. Zeng, Z. Qiu, A. Domınguez-Huerta, Z. Hearne, Z. Chen and
C.-J. Li, ACS Catal., 2017, 7, 510–519; (b) Z. Qiu, H. Zeng and C.-J. Li,
Acc. Chem. Res., 2020, 53, 2395–2413.
3 (a) D.-G. Yu, B.-J. Li and Z.-J. Shi, Acc. Chem. Res., 2010, 43,
1486–1495; (b) B. M. Rosen, K. W. Quasdorf, D. A. Wilson,
N. Zhang, A.-M. Resmerita, N. K. Garg and V. Percec, Chem. Rev.,
2011, 111, 1346–1416; (c) J. Cornella, C. Zarate and R. Martin,
Chem. Soc. Rev., 2014, 43, 8081–8097; (d) B. Su, Z.-C. Cao and
Z.-J. Shi, Acc. Chem. Res., 2015, 48, 886–896; (e) M. Tobisu and
N. Chatani, Acc. Chem. Res., 2015, 48, 1717–1726.
4 (a) K. Yoshino, T. Kohno, T. Morita and G. Tsukamoto, J. Med.
Chem., 1989, 32, 1528–1532; (b) E. A. Wydysh, S. M. Medghalchi,
A. Vadlamudi and C. A. Townsend, J. Med. Chem., 2009, 52,
3317–3327; (c) X. Chen, D. J. Kopecky, J. Mihalic, S. Jeffries,
X. Min, J. Heath, J. Deignan, S. Lai, Z. Fu, C. Guimaraes, S. Shen,
S. Li, S. Johnstone, S. Thibault, H. Xu, M. Cardozo, W. Shen,
N. Walker, F. Kayser and Z. Wang, J. Med. Chem., 2012, 55,
12 W. Liu, X. Yang, Y. Gao and C.-J. Li, J. Am. Chem. Soc., 2017, 139,
8621–8627.
13 (a) J. Yu, C.-J. Li and H. Zeng, Angew. Chem., Int. Ed., 2021, 60,
4043–4048; (b) Q. Dou, C.-J. Li and H. Zeng, Chem. Sci., 2020, 11,
5740–5744; (c) D. Cao, J. Yu, H. Zeng and C.-J. Li, J. Agric. Food
Chem., 2020, 68, 13200–13205; (d) Z. Wang, J. Niu, H. Zeng and C.-
J. Li, Org. Lett., 2019, 21, 7033–7037; (e) H. Zeng, D. Cao, Z. Qiu and
C.-J. Li, Angew. Chem., Int. Ed., 2018, 57, 3752–3757; ( f ) Z. Chen,
H. Zeng, S. A. Girard, F. Wang, N. Chen and C.-J. Li, Angew. Chem.,
Int. Ed., 2015, 54, 14487–14491; (g) H. Zeng, D. Cao, Z. Qiu and
C.-J. Li, ACS Catal., 2018, 8, 8873–8878; (h) H. Zeng, Z. Wang and
C.-J. Li, Angew. Chem., Int. Ed., 2019, 58, 2859–2863; (i) Z. Wang,
H. Zeng and C.-J. Li, Org. Lett., 2019, 21, 2302–2306; ( j) H. Zeng,
J. Yu and C.-J. Li, Chem. Commun., 2020, 56, 1239–1242; (k) Y. Lang,
C.-J. Li and H. Zeng, Synlett, 2021, 429–435.
´
´
3837–3851; (d) G. Nemeth, Z. Greff, A. Sipos, Z. Varga, R. Szekely,
´
´
´
M. Sebestyen, Z. Jaszay, S. Beni, Z. Nemes, J.-L. Pirat, J.-N. Volle,
D. Virieux, A. Gyuris, K. Kelemenics, E. Ay, J. Minarovits,
S. Szathmary, G. Keri and L. Orfi, J. Med. Chem., 2014, 57, 3939–3965.
´
´
´
+
´
´
5 T. Baumgartner and R. Reau, Chem. Rev., 2006, 106, 4681–4727.
6 (a) P. E. Goudriaan, P. W. N. M. van Leeuwen, M.-N. Birkholz and
J. N. H. Reek, Eur. J. Inorg. Chem., 2008, 2939–2958; (b) J. C. Zhang,
S. X. Cao, X. L. Yang and Y. F. Zhao, Chin. Chem. Lett., 2004, 15,
646–648; (c) W. Yang, B. Li, M. Zhang, S. Wang, Y. Ji, S. Dong, J. Feng
and S. Yuan, Chin. Chem. Lett., 2020, 31, 1313–1316; (d) Y.-C. Wang,
L.-Q. Liu, G.-M. Wang, H. Ouyang and Y.-J. Li, Green Chem., 2018, 20,
604–608; (e) Y.-Y. Xie, Y.-C. Wang, Y. He, D. C. Hu, H. S. Wang and
Y.-M. Pan, Green Chem., 2017, 19, 656–659.
14 J.-J. L. Fu, W. G. Bentrude and C. E. Griffin, J. Am. Chem. Soc., 1972,
94, 7717–7722.
15 A. Arbuzov, J. Russ. Phys. -Chem. Soc., 1906, 38, 687.
8432 | Chem. Commun., 2021, 57, 8429–8432
This journal is © The Royal Society of Chemistry 2021