11
Colorless crystals, 103 mg, 59% yield, mp 149
−
150 oC, Rf =
(t,
J
= 7.4 Hz, 2H), 7.31 (t,
J
= 6.9 Hz, 1H), 7.06 (d,
J =
ACCEPTED MANUSCRIPT
1
0.26 (silica gel plate, EA:PE = 1:5, v/v). H NMR (400
MHz, CDCl3) δ: 8.17 (d, = 7.6 Hz, 2H), 7.68 (t, = 7.4 Hz,
1H), 7.57 (t, = 7.7 Hz, 2H), 7.53 – 7.40 (m, 5H), 7.32 (t,
= 7.8 Hz, 1H), 7.27 – 7.21 (m, 1H), 7.11 (t, = 7.6 Hz, 1H),
6.69 (d,
= 8.1 Hz, 1H), 6.22 (s, 1H). 13C NMR (101 MHz,
7.7 Hz, 1H), 6.85 (d, J = 7.7 Hz, 1H), 6.45 (s, 1H), 6.11 (s,
J
J
1H), 4.78 (s, 2H), 2.27 (s, 3H). 13C NMR (101 MHz, CDCl3)
δ: 187.5, 141.1, 140.7, 135.9, 135.3, 134.6, 129.2, 129.2,
128.9, 127.9, 127.1, 126.3, 123.3, 115.9, 111.3, 65.7, 46.5,
21.9. IR (KBr, cm-1): 1692, 1328, 1175. HRMS (ESI) calcd
for C22H20NO3S+ [M+H+] m/z: 378.1158, found 378.1152.
J
J
J
J
CDCl3) δ: 187.4, 142.0, 135.8, 134.7, 133.4, 130.2, 130.0,
129.22, 129.16, 128.4, 126.8, 123.0, 119.1, 111.8, 66.0. IR
(KBr, cm-1): 1692, 1337, 1161. HRMS (ESI) calcd for
C20H16NO3S+ [M+H+] m/z: 350.0845, found 350.0838.
4.5.10. (3-Benzyl-2,2-dioxido-1,3-
dihydronaphtho[2,1-c]isothiazol-1-
yl)phenylmethanone (10j)
o
4.5.6. (1-Benzyl-5-methyl-2,2-dioxido-1,3-
dihydrobenzo[c]isothiazol-3-yl)phenylmethanone
(10f)
Colorless crystals, 61 mg. 30% yield, mp 195
−
197 C, Rf =
1
0.26 (silica gel plate, EA:PE = 1:5, v/v). H NMR (400
MHz, CDCl3) δ: 8.23 (d, = 7.6 Hz, 2H), 7.92 – 7.77 (m,
2H), 7.74 (t, = 7.4 Hz, 1H), 7.63 (t, = 7.7 Hz, 2H), 7.48
(d, = 7.3 Hz, 2H), 7.44 – 7.28 (m, 5H), 7.20 (d, = 8.0 Hz,
1H), 6.96 – 6.89 (m, 1H), 6.49 (s, 1H), 4.93 (d, = 16.7 Hz,
1H), 4.88 (d,
= 16.9 Hz, 1H). 13C NMR (101 MHz, CDCl3)
J
Colorless crystals, 89 mg, 47% yield, mp 153
−
155 oC, Rf =
J
J
1
0.29 (silica gel plate, EA:PE = 1:5, v/v). H NMR (400
MHz, CDCl3) δ: 8.17 (d, = 7.3 Hz, 2H), 7.70 (t, = 7.4 Hz,
1H), 7.59 (t, = 7.7 Hz, 2H), 7.43 (d, = 7.3 Hz, 2H), 7.36
(t, = 7.4 Hz, 2H), 7.30 (t, = 7.2 Hz, 1H), 7.04 (d, = 8.3
Hz, 1H), 7.00 (s, 1H), 6.52 (d, = 8.2 Hz, 1H), 6.11 (s, 1H),
4.79 (d, = 16.6 Hz, 1H), 4.75 (d, = 16.6 Hz, 1H), 2.27 (s,
J
J
J
J
J
J
J
J
J
J
J
δ: 187.4, 139.9, 135.9, 135.4, 134.7, 131.3, 129.8, 129.5,
129.3, 129.3, 129.3, 128.9, 128.3, 128.0, 127.2, 124.5,
122.2, 112.5, 111.8, 65.3, 47.5. IR (KBr, cm-1): 1678, 1343,
J
J
J
3H). 13C NMR (101 MHz, CDCl3) δ: 187.6, 138.9, 135.9,
135.2, 134.7, 132.3, 130.7, 129.2, 129.2, 128.8, 127.9,
127.2, 127.0, 119.0, 110.8, 65.9, 46.9, 20.9. IR (KBr, cm-1):
1692, 1328, 1175. HRMS (ESI) calcd for C22H19NNaO3S+
[M+Na+] m/z: 400.0978, found 400.0974.
1180. HRMS (ESI) calcd for C25H19NNaO3S+ [M+Na+] m/z
:
436.0978, found 436.0972.
4.5.11. 1-(1-Benzyl-4,6-dimethyl-2,2-dioxido-1,3-
dihydrobenzo[c]isothiazol-3-yl)ethan-1-one (10k)
Colorless crystals, 73 mg, 37% yield, mp 128
o
−
129 C, Rf =
1
4.5.7. (1-Benzyl-5-methoxy-2,2-dioxido-1,3-
dihydrobenzo[c]isothiazol-3-yl)phenylmethanone
(10g)
0.35 (silica gel plate, EA:PE = 1:5, v/v). H NMR (400
MHz, CDCl3) δ: 7.42 (d, = 7.2 Hz, 2H), 7.40 – 7.35 (m,
2H), 7.34 – 7.29 (m, 1H), 6.67 (s, 1H), 6.30 (s, 1H), 5.05 (s,
J
o
Colorless crystals, 36 mg, 18% yield, mp 150
−
151 C, Rf =
1H), 4.90 (d,
J = 16.5 Hz, 1H), 4.61 (d, J = 16.5 Hz, 1H),
1
2.29 (s, 3H), 2.23 (s, 3H), 2.12 (s, 3H). 13C NMR (101 MHz,
CDCl3) δ: 195.6, 140.9, 140.8, 135.6, 135.1, 128.9, 128.0,
127.2, 124.9, 114.1, 108.7, 70.6, 45.8, 27.8, 21.8, 18.7. IR
(KBr, cm-1): 1729, 1327, 1185. HRMS (ESI) calcd for
C18H20NO3S+ [M+H+] m/z: 330.1158, found 330.1161.
0.18 (silica gel plate, EA:PE = 1:5, v/v). H NMR (400
MHz, CDCl3) δ: 8.17 (d, = 7.4 Hz, 2H), 7.71 (t, = 7.4 Hz,
1H), 7.60 (t, = 7.7 Hz, 2H), 7.44 (d, = 7.4 Hz, 2H), 7.37
(t, = 7.4 Hz, 2H), 7.33 – 7.28 (m, 1H), 6.83 – 6.73 (m,
2H), 6.56 (d, = 8.7 Hz, 1H), 6.10 (s, 1H), 4.80 (d, = 16.3
Hz, 1H), 4.72 (d,
= 16.3 Hz, 1H), 3.73 (s, 3H). 13C NMR
J
J
J
J
J
J
J
J
(101 MHz, CDCl3) δ: 187.5, 155.6, 135.8, 135.4, 135.1,
134.7, 129.3, 129.2, 128.9, 127.9, 127.3, 120.8, 115.6,
112.7, 112.6, 66.2, 55.7, 48.1. IR (KBr, cm-1): 1693, 1327,
Acknowledgments
1179. HRMS (ESI) calcd for C22H20NO4S+ [M+H+] m/z
:
This work was supported by the National Natural Science
Foundation of China (No. 21572017 for J. X. Xu, and No.
21602010 for Z. H. Yang), the BUCT Fund for Discipline
Construction and Development (Project No. XK1533), and the
China Postdoctoral Science Foundation (No. 2016M600900).
394.1108, found 394.1102.
4.5.8. (1-Benzyl-4,6-dimethyl-2,2-dioxido-1,3-
dihydrobenzo[c]isothiazol-3-yl)phenylmethanone
(10h)
o
Colorless crystals, 62 mg, 32% yield, mp 187
−
187 C, Rf =
Supplementary Material
1
0.35 (silica gel plate, EA:PE = 1:5, v/v). H NMR (400
MHz, CDCl3) δ: 8.15 (d, = 7.6 Hz, 2H), 7.69 (t, = 7.4 Hz,
1H), 7.58 (t, = 7.7 Hz, 2H), 7.42 (d, = 7.3 Hz, 2H), 7.36
(t, = 7.5 Hz, 2H), 7.29 (t, = 7.2 Hz, 1H), 6.67 (s, 1H),
6.29 (s, 1H), 6.06 (s, 1H), 4.82 (d, = 16.7 Hz, 1H), 4.71 (d,
= 16.7 Hz, 1H), 2.22 (s, 3H), 2.03 (s, 3H). 13C NMR (101
J
J
1H and 13C NMR spectra of sulfonamides 12a-m and 13a-k,
diazosulfonamides 3a-m and 9a-k, and products 10a-k. The
doi: 10.1021/xxxxxx.
J
J
J
J
J
J
MHz, CDCl3) δ: 187.5, 141.2, 140.4, 136.0, 135.3, 135.1,
134.5, 129.2, 129.1, 128.8, 127.7, 127.0, 124.9, 115.5,
108.9, 65.0, 46.6, 21.8, 19.2. IR (KBr, cm-1): 1692, 1325,
References and notes
1. For selected reviews, see: (a) Cardin, D. J.; Cetinkaya, B.; Lappert, M.
F. Chem. Rev. 1972, 72, 545−574. (b) Padwa, A.; Krunpe, K. E.
Tetrahedron 1992, 48, 5385−5453. (c) Doyle, M. P.; Forbes, D. C.
Chem. Rev. 1998, 98, 911−936. (d) Doyle, M. P.; McKervey, M. A.;
Ye, T. Modern Catalytic Methods for Organic Synthesis with Diazo
Compounds; John Willey and Sons: New York, NY, 1998. (e) Davies,
H. M. L.; Beckwith, R. E. Chem. Rev. 2003, 103, 2861−2904. (f)
Davies, H. M. L.; Manning, J. R. Nature 2008, 451, 417−424. (g)
Zhang, Z.; Wang, J. Tetrahedron 2008, 64, 6577−6605. (h) Doyle, M.
P.; Duffy, R.; Ratnikov, M.; Zhou, L. Chem. Rev. 2010, 110, 704−724.
(i) Shao, Z.; Zhang, H. Chem. Soc. Rev. 2012, 41, 560−572. (j) Xiao,
Q.; Zhang, Y.; Wang, J. Acc. Chem. Res. 2013, 46, 236−247. (k) Dötz
1170. HRMS (ESI) calcd for C23H21NNaO3S+ [M+Na+] m/z
:
414.1134, found 414.1128.
4.5.9. (1-Benzyl-6-methyl-2,2-dioxido-1,3-
dihydrobenzo[c]isothiazol-3-
yl)phenylmethanone(10i)
Colorless crystals, 57 mg, 30% yield, mp 156
o
−
158 C, Rf =
1
0.29 (silica gel plate, EA:PE = 1:5, v/v). H NMR (400
MHz, CDCl3) δ: 8.17 (d, = 7.4 Hz, 2H), 7.70 (t, = 7.4 Hz,
1H), 7.58 (t, = 7.7 Hz, 2H), 7.44 (d, = 7.4 Hz, 2H), 7.38
J
J
J
J