Please do not adjust margins
Page 5 of 6
Chemical Science
Journal Name
ARTICLE
3498–3501; (h) A. Joshi, D. C. Mohan, S. Adimurthy, J. Org.
Chem. 2016, 81, 9461–9469; (i) A. Joshi, D. C. Mohan and S.
Adimurthy, Org. Lett. 2016, 18, 464–467; (j) R. Adam, S.
Alom, B. Abarca and R. Ballesteros, Tetrahedron, 2016, 72,
8436–8441; (k) H. Kim, S. Kim, J. Kim, J.-Y. Son, K. Um and P.
H. Lee, Org. Lett. 2017, 19, 5677–5680; (l) S. Roy, S. K. Das, B.
Chattopadhyay, Angew. Chem. Int. Ed. 2018, 57, 2238–2243.
For selected reports on transannulation of N-sulfonyl
triazoles, see: (a) T. Horneff, S. Chuprakov, N. Chernyak, V.
Gevorgyan and V. V. Fokin, J. Am. Chem. Soc. 2008, 130,
14972–14974; (b) T. Miura, M. Yamauchi, M. Murakami,
Chem. Commun. 2009, 1470–1471; c) B. Chattopadhyay and
V. Gevorgyan, Org. Lett. 2011, 13, 3746–3749; (d) B. T. Parr,
S. A. Green and H. M. L. Davies, J. Am. Chem. Soc. 2013, 135,
4716–4718; (e) J. E. Spangler and H. M. L. Davies, J. Am.
Chem. Soc. 2013, 135, 6802–6805; f) J. S. Alford, J. E.
Spangler and H. M. L. Davies, J. Am. Chem. Soc. 2013, 135,
11712-11715; (g) B. T. Parr and H. M. L. Davies, Angew.
Chem. Int. Ed., 2013, 52, 10044–10047; Angew. Chem., 2013,
125, 10228–10231; (h) M. Zibinsky and V. V. Fokin, Angew.
Chem. Int. Ed. 2013, 52, 1507–1510; Angew. Chem., 2013,
125, 1547–1550; (i) S. Chuprakov, S. W. Kwok and V. V.
DOI: 10.1039/C9SC02448D
Ed., 2018, 57, 7151–7155.
M. Ratushnyy, M. Kamenova and V. Gevorgyan, Chem. Sci.
2018, 9, 7193–7197.
8
9
Harsh UVC irradiation by Hg-Xe lamp combined with
monochromators or fillers was reproted. (a) M. Kuzaj, H,
Lüerssen and C. Wentrup, Angew. Chem. Int. Ed., 1986, 25,
480–482; (b) K. Komatsu, N. Ichikawa and H. Tomioka, J. Am.
Chem. Soc. 1993, 115, 8621–8626; (c) A. Ignatchenko and H.
E. Zimmerman, J. Org. Chem. 1999, 64, 6635–6645; (d) A.
Kuhn, C. Plüg and C. Wentrup, J. Am. Chem. Soc. 2000, 122,
1945–1948; (e) C. Plüg, A. Kuhn and C. Wentrup, J. Chem.
Soc. Perk. T. 1, 2002, 1366–1368; (f) H. G. Aderson, P.
Bednarek and C. Wentrup, J. Phys. Org. Chem. 2003, 16,
519–524; (g) N. Fu, A. D. Allen, S. Kobayashi, P. A. Sequeira,
M. Shang, T. T. Tidewell and M. Mishima, J. Am. Chem. Soc.
2007, 129, 6210–6215. For recent report on photo-redox
transformation of benzotriazoles, see: (h) M. Teders, A.
Gómez-Suárez, L. Pitzer, M. N. Hopkinson and F. Glorius,
Angew. Chem. Int. Ed. 2017, 56, 902–906; (i) M. Teders, L.
Pitzer, S. Buss and F. Glorius, ACS Catal. 2017, 7, 4053–4056.
4
Fokin, J. Am. Chem. Soc. 2013, 135, 4652–4655; j) T. Miura, T. 10 (a) I. D. Jurberg and H. M. L. Davies, Chem. Sci. 2018, 9,
Tanaka, K. Hiraga, S. G. Stewart and M. Murakami, J. Am.
Chem. Soc. 2013, 135, 13652–13655; (k) T. Miura, K. Hiraga,
T. Biyajima, T. Nakamuro and M. Murakami, Org. Lett. 2013,
15, 3298–3301; (l) E. E. Schultz and R. Sarpong, J. Am. Chem.
Soc. 2013, 135, 4696–4699; (m) Y. Shi and V. Gevorgyan, Org.
Lett. 2013, 15, 5394–5396; (n) T. Miura, Y. Funakoshi and M.
Murakami, J. Am. Chem. Soc. 2014, 136, 2272–2275; (o) C.
Kim, S. Park, D. Eom, B. Seo and P. H. Lee, Org. Lett. 2014,
16, 1900–1903; (p) J. Yang, C. Zhu, X. Tang and M. Shi,
Angew. Chem. Int. Ed., 2014, 53, 5142-5146; Angew. Chem.,
2014, 126, 5242–5246; (q) H. Shang, Y. Wang, Y. Tian, J. Feng
and Y. Tang, Angew. Chem. Int. Ed. 2014, 53, 5662–5666; r)
K. Chen, Z.-Z. Zhu, Y.-S. Zhang, X.-Y. Tang and M. Shi, Angew.
5112–5118; (b) T. Xiao, M. Mei, Y. He, L. Zhou, Chem.
Commun. 2018, 54, 8865-8868; (c) R. Hommelsheim, Y. Guo,
Z. Yang, C. Empel, R. M. Koenigs, Angew. Chem. Int. Ed. 2019,
58, 1203-1207; (d) Ł. W. Ciszewski, K. Rybicka-Jasińska and D.
Gryko, Org. Biomol. Chem. 2019, 17, 432-448; (e) F. He and
R. M. Koenigs, Chem. Commun 2019, 55, 4881-4884; (f) J.
Yang, J. Wang, H. Huang, G. Qin, Y. Jiang and T. Xiao, Org.
Lett. 2019, 21, 2654-2657; (g) S. Jana and R. M. Koenigs,
Asian J. Org. Chem. doi.org/10.1002/ajoc.201900099; (h) Z.
Yang, Y. Guo and R. M. Koenigs, Chem. Eur. J.
doi.org/10.1002/chem.201900597; i) X. Zhang, C. Du, H.
Zhang, X. Li, Y. Wang, J. Niu and M. Song, Synthesis 2019, 51,
889-898.
Chem. Int. Ed. 2014, 53, 6645–6649; t) F. Medina, C. Besnard 11 During manuscript preparation, a related work on thermal
and J. Lacour, Org. Lett. 2014, 16, 3232–3235; (u) V. N. G.
Lindsay, H. M.-F. Viart and R. Sarpong, J. Am. Chem. Soc.
2015, 137, 8368–8371; (v) W. Cheng, Y. Tang, Z. Xu and C. Li,
arylation of mostly activated pyridotriazoles has been
reported, see: (a) C. Dong, X. Wang, Z. Pei and R. Shen. Org.
Lett. 2019, 21, 4148-4152.
Org. Lett. 2016, 18, 6168–6171; (w) Y. Li, R. Zhang, A. Ali, J. 12 For application and importance of triarylmethanes, see: (a)
Zhang, X. Bi and J. Fu. Org. Lett. 2017, 19, 3087–3090; (x) L.
Fu, H. M. L. Davis and R. Sarpong, Org. Lett. 2017, 19, 1504–
1507; (y) W. Chen, Y. Bai, Y. Luo, P. Xu. Org. Lett. 2017, 19,
364–367; (z) D. Yadagiri, M. Chaitanya and A. C. S. Reddy, P.
Anbarasan, Org. Lett. 2018, 20, 3762–3765.
For selected reports on X-H insertions of N-sulfonyl triazoles,
see: (a) S. Chuprakov, J. A. Malik, M. Zibinsky and V. V. Fokin,
J. Am. Chem. Soc. 2011, 133, 10352–10355; (b) T. Miura, T.
Biyajima, T. Fujii and M. Murakami, J. Am. Chem. Soc. 2012,
134, 194–196; (c) T. Miura, T. Tanaka, T. Biyajima, A. Yada
and M. Murakami, Angew. Chem. Int. Ed., 2013, 52, 3883–
3886; Angew. Chem., 2013, 125, 3975–3978; (d) S.
Chuprakov, B. T. Worrell, N. Selander, R. K. Sit and V. V.
Fokin, J. Am. Chem. Soc. 2014, 136, 195–202; (e) T. Miura, Q.
Zhao and M. Murakami, Angew. Chem. Int. Ed., 2017, 56,
16645–16649.
For selected reports on cyclopropanation of N-sulfonyl
triazoles, see: a) S. Chuprakov, S. W. Kwok, L. Zhang, L.
Lercher and V. V. Fokin, J. Am. Chem. Soc. 2009, 131, 18034–
18035; (b) N. Grimster, L. Zhang and V. V. Fokin, J. Am. Chem.
Soc. 2010, 132, 2510–2511; (c) J. S. Alford and H. M. L.
Davies, Org. Lett. 2012, 14, 6020–6023; (d) J. C. Culhane and
V. V. Fokin, Org. Lett. 2011, 13, 4578–4580.
M. Irie, J. Am. Chem. Soc. 1983, 105, 2078–2079; (b) D.
Duxbury, Chem. Rev. 1993, 93, 381–433; (c) M. S.
Shchepinov, Chem. Soc. Rev. 2003, 32, 170–180; (d) R. S.
Dothager, K. S. Putt, B. J. Allen, B. J. Leslie, V. Nesterenko and
P. J. Hergenrother, J. Am. Chem. Soc. 2005, 127, 8686–8696;
(e) V. Nair, S. Thomas, S. C. Mathew, K. G. Abhilash,
Tetrahedron, 2006, 62, 6731–6747; f) A. C. Bhasikuttan, J.
Mohanty, W. M. Nau and H. Pal, Angew. Chem. Int. Ed. 2007,
46, 4120–4122; (g) S. K. Das, G. Panda, V. Chaturvedi, Y.S.
Manju, A. K. Gaikwad and S. Sinha, Bioorg. Med. Chem. Lett.
2007, 17, 5586–5589; (h) H. Abe, J. Wang, K. Furukawa, K.
Oki, M. Uda, S. Tsuneda and Y. Ito, Bioconjugate Chem. 2008,
19, 1219–1226; (i) H. N. Kim, M. H. Lee, H. J. Kim, J. S. Kim
and J. Yoon, Chem. Soc. Rev. 2008, 37, 1465–1472; (j) M.
Beija, C. A. M. Afonso and . M. G. Martinho, Chem. Soc. Rev.
2009, 38, 2410–2433. For the synthesis of triarylmethanes,
selected examples: (k) T. Niwa, H. Yorimitsu and K. Oshima,
Org. Lett. 2007, 9, 2373-2375; (l) Y. Xia, F. Hu, Z. Liu, P. Qu, R.
Ge, C. Ma, Y. Zhang and J. Wang, Org. Lett. 2013, 15, 1784–
1787; (m) M. Nambo and C. M. Crudden, Angew. Chem. Int.
Ed. 2014, 53, 742–746; (n) X. Cao, S. Sha, B. Kim, C. Morgan,
R. Huang, C. Yang and P. J. Walsh, Chem. Sci. 2016, 7, 611–
618.
5
6
7
For selected transformations on N-sulfonyl triazoles, see: (a) 13 For nucleophilic addition of electron-rich arenes to rhodium
N. Selander, B. T. Worrell, S. Chuprakov, S. Velaparthi and V.
V. Fokin, J. Am. Chem. Soc. 2012, 134, 14670–14673; (b) D.
Yadagiri, A. C. S. Reddy and P. Anbarasan, Chem. Sci. 2016, 7,
carbenoids, see: (a) D. Yadagiri and P. Anbarasan, Org. Lett.
2014, 16, 2510–2513; (b) S. Shin, Y. Park, C. Kim, J.Son, P.
Lee, J. Org. Chem. 2015, 80, 5859–5869. We were
This journal is © The Royal Society of Chemistry 20xx
J. Name., 2013, 00, 1-3 | 5
Please do not adjust margins