Rh(III)-Catalyzed C-H Amidation with N-hydroxycarbamates: A. new Entry to N-Carbamate Protected Arylamines
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- Αρσένιος Αλεξάκης
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1 Rh(III)-Catalyzed C-H Amidation with N-hydroxycarbamates: A new Entry to N-Carbamate Protected Arylamines Bing Zhou,* Juanjuan Du, Yaxi Yang,* Huijin Feng, Yuanchao Li Shanghai Institute of Materia Medica, Chinese Academy of Sciences, 555 Zu Chong Zhi Road, Shanghai , PR China zhoubing2012@hotmail.com; spyyx@163.com Table of contents: General Methods and Materials..1 X-ray structure of 3a 2 Experimental Procedures and Characterizations 2 1 H and 13 C NMR Spectra of Compounds..16 General methods: Mass spectra and high-resolution mass spectra were measured on a Finnigan MAT-95 mass spectrometer. 1 H and 13 C NMR spectra were determined on Bruker AM-300, Bruker AM-400, Bruker AM-500 instruments using tetramethylsilane as internal reference. Data are presented as follows: chemical shift, multiplicity (s = singlet, br s = broad singlet, d = doublet, br d = broad doublet, t = triplet, m = multiplet), J = coupling constant in hertz (Hz). Silica gel 60H ( mesh) manufactured by Qingdao Haiyang Chemical Group Co. (China) was used for general chromatography. Materials: 2-Phenylpyridine, tert-butyl N-hydroxy carbamate, Benzyl N-hydroxy carbamate, Acetohydroxamic acid and silver carbonate was purchased from Adamas-beta and used without further purification. [Cp*RhCl 2 ] 2 S1, [Cp*Rh(MeCN) 3 ][SbF 6 ] 2 S2 and other hydroxycarbamates S3 were synthesized according to published procedures. 1
2 X-ray structure of 3a Experimental Procedures and Characterizations: [Cp*Rh(MeCN) 3 ][SbF 6 ] 2 (2.5mol%), 2-Phenylpyridine (1) (0.2mmol), Benzyl N-hydroxy carbamate (2a) (0.24 mmol), Ag 2 CO 3 (0.3 mmol), THF (1 ml) were added in a sealed tube. It was stirred at 100 for 10h. The volatile was removed under reduced pressure and the crude product was purified by column chromatography on silica gel. benzyl 2-(pyridin-2-yl)phenylcarbamate(3a) chromatography on silica gel in 77% yield. 2
3 1 H NMR (300 MHz, CDCl 3 ) δ (s, 1H), (m, 1H), 8.34 (d, J = 8.3 Hz, 1H), 7.82 (m, 1H), 7.71 (d, J = 8.1 Hz, 1H), 7.62 (dd, J = 7.9, 1.4 Hz, 1H), (m, 6H), (m, 1H), 7.13 (m, 1H), 5.21 (s, 2H). 13 C NMR (126 MHz, CDCl 3 ) δ 158.2, 153.9, 147.7, 137.7, 137.6, 136.6, 130.1, 129.0, 128.5, 128.2, 128.1, 122.9, 122.7, 121.8, 120.6, HRMS (EI) calcd. for C 19 H 16 N 2 O 2 [M]+ : Found: benzyl 5-methyl-2-(pyridin-2-yl)phenylcarbamate(3b) chromatography on silica gel in 70% yield. 1 H NMR (300 MHz, CDCl 3 ) δ (s, 1H), 8.61 (d, J = 4.1 Hz, 1H), 8.20 (s, 1H), (m, 1H), 7.68 (d, J = 8.0 Hz, 1H), 7.53 (d, J = 8.0 Hz, 1H), 7.38 (m, 5H), 7.21 (m, 1H), 6.94 (d, J = 8.0 Hz, 1H), 5.21 (s, 2H), 2.41 (s, 3H). 13 C NMR (126 MHz, CDCl 3 ) δ 158.3, 154.0, 147.6, 140.4, 137.7, 137.5, 136.7, 128.7, 128.5, 128.1, 128.1, 123.6, 122.6, 122.5, 121.4, 120.9, 66.5, HRMS (EI) calcd. for C 20 H 18 N 2 O 2 [M]+ : Found: benzyl 5-methoxy-2-(pyridin-2-yl)phenylcarbamate(3c) chromatography on silica gel in 80% yield. 1 H NMR (300 MHz, CDCl 3 ) δ (s, 1H), 8.59 (d, J = 5.6 Hz, 1H), 8.05 (s, 1H), 7.76 (t, J = 7.8 Hz, 1H), 7.65 (d, J = 7.7 Hz, 1H), 7.58 (d, J = 8.8 Hz, 1H),
4 (m, 5H), (m, 1H), 6.67 (dd, J = 8.8, 1.9 Hz, 1H), 5.22 (s, 2H), 3.88 (s, 3H). 13 C NMR (126 MHz, CDCl 3 ) δ 161.0, 158.1, 154.0, 147.4, 139.6, 137.5, 136.6, 129.8, 128.5, 128.1, 128.1, 121.9, 121.0, 117.5, 109.6, 104.4, 66.5, HRMS (EI) calcd. for C 20 H 18 N 2 O 3 [M]+ : Found: methyl 3-(benzyloxycarbonylamino)-4-(pyridin-2-yl)benzoate(3d) chromatography on silica gel in 92% yield. 1 H NMR (400 MHz, CDCl 3 ) δ (s, 1H), 9.02 (s, 1H), 8.69 (d, J = 4.9 Hz, 1H), 7.87 (td, J = 7.9, 1.8 Hz, 1H), 7.82 (dd, J = 8.2, 1.7 Hz, 1H), 7.77 (d, J = 8.1 Hz, 1H), 7.72 (d, J = 8.2 Hz, 1H), 7.45 (d, J = 7.2 Hz, 2H), 7.36 (m, 4H), 5.25 (s, 2H), 3.96 (s, 3H). 13 C NMR (126 MHz, CDCl 3 ) δ 166.7, 157.2, 153.8, 147.9, 137.9, 137.8, 136.5, 131.4, 128.9, 128.5, 128.2, 128.2, 123.7, 123.3, 122.5, 121.6, 66.7, HRMS (EI) calcd. for C 21 H 18 N 2 O 4 [M]+ : Found: benzyl 5-chloro-2-(pyridin-2-yl)phenylcarbamate(3e) chromatography on silica gel in 70% yield. 1 H NMR (300 MHz, CDCl 3 ) δ (s, 1H), 8.63 (d, J = 4.3 Hz, 1H), 8.46 (s, 1H), 7.81 (t, J = 7.5 Hz, 1H), 7.67 (d, J = 8.1 Hz, 1H), 7.55 (d, J = 8.5 Hz, 1H), (m, 5H), 7.26 (t, J = 5.9 Hz, 1H), 7.08 (d, J = 8.5 Hz, 1H), 5.22 (s, 2H). 13 C NMR (126 MHz, CDCl 3 ) δ 157.3, 153.7, 147.7, 139.0, 137.8, 136.4, 136.0, 129.8, 128.6, 4
5 128.3, 128.2, 123.3, 122.7, 122.6, 122.0, 120.2, HRMS (EI) calcd. for C 19 H 15 ClN 2 O 2 [M]+ : Found: benzyl 5-bromo-2-(pyridin-2-yl)phenylcarbamate(3f) chromatography on silica gel in 70% yield. 1 H NMR (300 MHz, CDCl 3 ) δ (s, 1H), 8.62 (d, J = 6.0 Hz, 2H), 7.81 (t, J = 7.8 Hz, 1H), 7.67 (d, J = 8.1 Hz, 1H), 7.40 (m, 6H), (m, 2H), 5.22 (s, 2H). 13 C NMR (126 MHz, CDCl 3 ) δ 157.3, 153.7, 147.7, 139.0, 137.8, 136.4, 130.0, 128.6, 128.3, 128.2, 125.6, 124.2, 123.7, 123.1, 122.6, 122.1, HRMS (EI) calcd. for C 19 H 15 BrN 2 O 2 [M]+ : Found: benzyl 4-methyl-2-(pyridin-2-yl)phenylcarbamate(3g) chromatography on silica gel in 64% yield. 1 H NMR (400 MHz, CDCl 3 ) δ (s, 1H), (m, 1H), 8.22 (d, J = 8.3 Hz, 1H), 7.82 (td, J = 7.8, 1.9 Hz, 1H), 7.71 (d, J = 8.1 Hz, 1H), (m, 6H), (m, 2H), 5.22 (s, 2H), 2.39 (s, 3H). 13 C NMR (101 MHz, CDCl 3 ) δ 158.2, 154.0, 147.7, 137.5, 136.7, 135.0, 132.1, 130.6, 129.4, 128.5, 128.2, 128.0, 122.9, 121.7, 120.7, 66.5, HRMS (EI) calcd. for C 20 H 18 N 2 O 2 [M]+ : Found:
6 benzyl 4-methoxy-2-(pyridin-2-yl)phenylcarbamate(3h) chromatography on silica gel in 60% yield. 1 H NMR (400 MHz, CDCl 3 ) δ (s, 1H), 8.67 (d, J = 4.9 Hz, 1H), 8.22 (d, J = 8.8 Hz, 1H), 7.84 (td, J = 7.9, 1.8 Hz, 1H), 7.69 (d, J = 8.0 Hz, 1H), (m, 5H), 7.28 (m, 1H), 7.16 (d, J = 2.9 Hz, 1H), 7.00 (dd, J = 9.1, 2.9 Hz, 1H), 5.20 (s, 2H), 3.87 (s, 3H). 13 C NMR (126 MHz, CDCl 3 ) δ 159.4, 156.5, 155.5, 149.3, 139.0, 138.2, 132.3, 129.9, 129.6, 129.4, 124.4, 123.4, 116.3, 116.2, 67.9, HRMS (EI) calcd. for C 20 H 18 N 2 O 3 [M]+ : Found: benzyl 4-chloro-2-(pyridin-2-yl)phenylcarbamate(3i) chromatography on silica gel in 54% yield. 1 H NMR (400 MHz, CDCl 3 ) δ (s, 1H), 8.68 (d, J = 4.3 Hz, 1H), 8.33 (d, J = 8.8 Hz, 1H), 7.86 (td, J = 7.8, 1.8 Hz, 1H), 7.71 (d, J = 8.1 Hz, 1H), 7.61 (d, J = 2.5 Hz, 1H), (m, 6H), 7.31 (ddd, J = 7.5, 4.9, 0.9 Hz, 1H), 5.22 (s, 2H). 13 C NMR (126 MHz, CDCl 3 ) δ 156.9, 153.8, 147.9, 137.9, 136.5, 136.4, 129.8, 128.6, 128.5, 128.2, 128.2, 127.7, 122.9, 122.4, 122.0, HRMS (EI) calcd. for C 19 H 15 ClN 2 O 2 [M]+ : Found:
7 benzyl 3-methyl-2-(pyridin-2-yl)phenylcarbamate(3j) chromatography on silica gel in 65% yield. 1 H NMR (400 MHz, CDCl 3 ) δ 8.76 (d, J = 4.3 Hz, 1H), 7.97 (d, J = 7.2 Hz, 1H), (m, 2H), (m, 8H), 7.05 (d, J = 7.6 Hz, 1H), 5.13 (s, 2H), 2.18 (s, 3H). 13 C NMR (126 MHz, CDCl 3 ) δ 156.7, 153.6, 149.8, 136.9, 136.3, 136.2, 135.6, 128.9, 128.5, 128.2, 128.2, 126.2, 125.8, 122.4, 66.7, HRMS (EI) calcd. for C 20 H 18 N 2 O 2 [M]+ : Found: benzyl 2-(pyridin-2-yl)thiophen-3-ylcarbamate(3k) chromatography on silica gel in 65% yield. 1 H NMR (300 MHz, CDCl 3 ) δ (s, 1H), (m, 1H), 7.97 (s, 1H), (m, 1H), (m, 6H), (m, 1H), (m, 1H), 5.25 (s, 2H). 13 C NMR (101 MHz, CDCl 3 ) δ 154.1, 153.6, 147.9, 138.5, 137.0, 136.4, 128.5, 128.2, 128.2, 124.6, 122.9, 120.3, 120.1, 118.3, HRMS (EI) calcd. for C 17 H 14 N 2 O 2 S [M]+ : Found: benzyl 2-(3-methylpyridin-2-yl)phenylcarbamate(3l) chromatography on silica gel in 55% yield. 1 H NMR (400 MHz, CDCl 3 ) δ 8.54 (d, J = 3.8 Hz, 1H), 8.23 (d, J = 22.1 Hz, 2H), 7.68 (d, J = 7.7 Hz, 1H), (m, 6H), 7.25 (m, 2H), 7.15 (td, J = 7.5, 1.0 Hz, 7
8 1H), 5.16 (s, 2H), 2.30 (s, 3H). 13 C NMR (101 MHz, CDCl 3 ) δ 156.3, 153.5, 146.6, 139.6, 136.2, 135.6, 132.4, 129.9, 129.1, 128.4, 128.2, 128.1, 122.7, 122.5, 66.7, HRMS (EI) calcd. for C 20 H 18 N 2 O 2 [M]+ : Found: benzyl 2-(4-methylpyridin-2-yl)phenylcarbamate(3m) chromatography on silica gel in 50% yield. 1 H NMR (400 MHz, CDCl 3 ) δ (s, 1H), 8.52 (d, J = 5.1 Hz, 1H), 8.34 (d, J = 8.3 Hz, 1H), 7.63 (dd, J = 7.9, 1.4 Hz, 1H), 7.54 (s, 1H), (m, 6H), 7.13 (m, 2H), 5.23 (s, 2H), 2.45 (s, 3H). 13 C NMR (126 MHz, CDCl 3 ) δ 157.9, 153.9, 148.8, 147.5, 137.7, 136.6, 129.8, 128.8, 128.4, 128.1, 128.0, 123.7, 122.9, 122.6, 120.5, 66.5, HRMS (EI) calcd. for C 20 H 18 N 2 O 2 [M]+ : Found: benzyl 2-(5-methylpyridin-2-yl)phenylcarbamate(3n) chromatography on silica gel in 60% yield. 1 H NMR (400 MHz, CDCl 3 ) δ (s, 1H), 8.50 (s, 1H), 8.33 (d, J = 8.2 Hz, 1H), 7.63 (m, 3H), (m, 6H), (m, 1H), 5.23 (s, 2H), 2.40 (s, 3H). 13 C NMR (126 MHz, CDCl 3 ) δ 155.3, 153.9, 148.0, 138.3, 137.4, 136.6, 131.5, 129.7, 128.7, 128.4, 128.2, 128.0, 122.7, 122.4, 120.6, 66.5, HRMS (EI) calcd. for C 20 H 18 N 2 O 2 [M]+ : Found:
9 benzyl 2-(6-methylpyridin-2-yl)phenylcarbamate(3o) chromatography on silica gel in 50% yield. 1 H NMR (400 MHz, CDCl 3 ) δ (s, 1H), 8.37 (d, J = 8.3 Hz, 1H), 7.72 (t, J = 7.8 Hz, 1H), 7.68 (dd, J = 7.9, 1.5 Hz, 1H), 7.56 (d, J = 8.0 Hz, 1H), (m, 6H), 7.13 (m, 2H), 5.25 (s, 2H), 2.63 (s, 3H). 13 C NMR (126 MHz, CDCl 3 ) δ 158.9, 157.8, 155.3, 139.4, 139.2, 138.2, 131.3, 130.0, 129.8, 129.3, 129.1, 123.8, 122.6, 121.5, 121.0, 67.7, HRMS (EI) calcd. for C 20 H 18 N 2 O 2 [M]+ : Found: benzyl 2-(5-chloropyridin-2-yl)phenylcarbamate(3p) chromatography on silica gel in 56% yield. 1 H NMR (400 MHz, CDCl 3 ) δ (s, 1H), 8.63 (d, J = 2.1 Hz, 1H), 8.35 (d, J = 8.3 Hz, 1H), 7.81 (dd, J = 8.6, 2.5 Hz, 1H), 7.68 (d, J = 8.6 Hz, 1H), 7.59 (dd, J = 7.9, 1.4 Hz, 1H), (m, 6H), (m, 1H), 5.22 (s, 2H). 13 C NMR (126 MHz, CDCl 3 ) δ 156.2, 153.8, 146.6, 137.5, 137.4, 136.4, 130.4, 130.3, 128.9, 128.5, 128.3, 128.1, 123.7, 122.8, 120.7, HRMS (EI) calcd. for C 19 H 15 ClN 2 O 2 [M]+ : Found:
10 benzyl benzo[h]quinolin-10-ylcarbamate(3q) chromatography on silica gel in 53% yield. 1 H NMR (400 MHz, CDCl 3 ) δ 8.96 (dd, J = 4.5, 1.8 Hz, 1H), 8.84 (d, J = 8.1 Hz, 1H), 8.24 (dd, J = 8.0, 1.8 Hz, 1H), 7.82 (d, J = 8.8 Hz, 1H), 7.72 (t, J = 7.9 Hz, 1H), 7.66 (d, J = 8.8 Hz, 1H), 7.60 (d, J = 7.8 Hz, 1H), 7.55 (dd, J = 7.9, 4.6 Hz, 3H), 7.43 (t, J = 7.4 Hz, 2H), (m, 1H), 5.36 (s, 2H). 13 C NMR (101 MHz, CDCl 3 ) δ 154.4, 147.8, 145.9, 139.5, 136.9, 136.3, 135.0, 129.2, 128.8, 128.5, 128.0, 127.9, 127.3, 125.1, 122.0, 120.6, 117.3, 116.6, HRMS (EI) calcd. for C 21 H 16 N 2 O 2 [M]+ : Found: benzyl 2-(pyrimidin-2-yl)phenylcarbamate(3r) chromatography on silica gel in 60% yield. 1 H NMR (400 MHz, CDCl 3 ) δ (s, 1H), 8.85 (d, J = 4.9 Hz, 2H), 8.58 (dd, J = 8.1, 1.7 Hz, 1H), 8.48 (d, J = 8.3 Hz, 1H), (m, 3H), (m, 3H), 7.22 (t, J = 4.9 Hz, 1H), (m, 1H), 5.27 (s, 2H). 13 C NMR (126 MHz, CDCl 3 ) δ 165.0, 156.4, 153.8, 139.8, 136.6, 132.0, 130.6, 128.5, 128.2, 128.1, 122.4, 122.2, 119.6, 118.3, HRMS (EI) calcd. for C 18 H 15 N 3 O 2 [M]+ : Found: benzyl 3-methyl-2-(pyrimidin-2-yl)phenylcarbamate(3s) chromatography on silica gel in 64% yield. 10
11 1 H NMR (400 MHz, CDCl 3 ) δ 8.91 (d, J = 4.9 Hz, 1H), 8.85 (s, 1H), 7.99 (s, 1H), 7.38 (m, 4H), 7.34 (m, 2H), (m, 1H), 7.07 (d, J = 7.5 Hz, 1H), 5.15 (s, 2H), 2.35 (s, 3H). 13 C NMR (101 MHz, CDCl 3 ) δ 165.6, 156.9, 153.5, 137.9, 136.2, 136.0, 129.6, 128.4, 128.2, 128.1, 126.3, 118.8, 66.7, HRMS (EI) calcd. For C 19 H 17 N 3 O 2 [M]+ : Found: benzyl 2-(1H-pyrazol-1-yl)phenylcarbamate(3t) chromatography on silica gel in 46% yield. 1 H NMR (400 MHz, CDCl 3 ) δ 9.66 (s, 1H), 8.34 (d, J = 8.0 Hz, 1H), 7.81 (dd, J = 5.5, 2.1 Hz, 2H), (m, 6H), 7.31 (dd, J = 8.0, 1.4 Hz, 1H), 7.14 (td, J = 7.9, 1.4 Hz, 1H), 6.50 (t, J = 2.2 Hz, 1H), 5.21 (s, 2H). 13 C NMR (126 MHz, CDCl 3 ) δ 153.5, 141.3, 136.2, 131.9, 130.0, 128.5, 128.3, 128.2, 128.1, 123.1, 122.6, 121.3, 107.1, HRMS (EI) calcd. For C 17 H 15 N 3 O 2 [M]+ : Found: (E)-benzyl 2-(1-(methoxyimino)ethyl)phenylcarbamate(3u) chromatography on silica gel in 55% yield. 1 H NMR (400 MHz, CDCl 3 ) δ (s, 1H), 8.33 (d, J = 8.3 Hz, 1H), (m, 7H), (m, 1H), 5.25 (s, 2H), 4.04 (s, 3H), 2.31 (s, 3H). 13 C NMR (101 MHz, CDCl 3 ) δ 156.3, 153.7, 136.9, 136.5, 129.7, 128.4, 128.3, 128.0, 127.8, 122.3, 122.2, 119.6, 66.4, 62.2, HRMS (EI) calcd. For C 17 H 18 N 2 O 3 [M]+ : Found:
12 (E)-benzyl 2-(1-(methoxyimino)ethyl)-5-methylphenylcarbamate(3v) chromatography on silica gel in 60% yield. 1 H NMR (300 MHz, CDCl 3 ) δ (s, 1H), 8.15 (s, 1H), 7.36 (m, 6H), 6.87 (d, J = 8.1 Hz, 1H), 5.22 (s, 2H), 4.00 (s, 3H), 2.36 (s, 3H), 2.26 (s, 3H). 13 C NMR (151 MHz, CDCl 3 ) δ 156.4, 153.8, 140.1, 136.9, 136.7, 128.5, 128.3, 128.0, 127.8, 123.1, 120.1, 119.6, 66.4, 62.2, 21.6, HRMS (EI) calcd. For C 18 H 20 N 2 O 3 [M]+ : Found: (E)-benzyl 5-bromo-2-(1-(methoxyimino)ethyl)phenylcarbamate(3w) chromatography on silica gel in 44% yield. 1 H NMR (300 MHz, CDCl 3 ) δ (s, 1H), 8.57 (d, J = 1.8 Hz, 1H), 7.36 (m, 6H), 7.17 (dd, J = 8.5, 2.0 Hz, 1H), 5.22 (s, 2H), 4.01 (s, 3H), 2.25 (s, 3H). 13 C NMR (101 MHz, CDCl 3 ) δ 155.9, 153.5, 138.3, 136.3, 129.5, 128.5, 128.1, 127.8, 125.2, 123.9, 122.2, 120.7, 66.7, 62.4, HRMS (EI) calcd. for C 17 H 17 BrN 2 O 3 [M]+ : Found: methoxybenzyl 2-(pyridin-2-yl)phenylcarbamate(3x) 12
13 chromatography on silica gel in 70% yield. 1 H NMR (400 MHz, CDCl 3 ) δ (s, 1H), 8.66 (d, J = 3.9 Hz, 1H), 8.36 (d, J = 8.1 Hz, 1H), 7.83 (td, J = 7.8, 1.9 Hz, 1H), 7.72 (d, J = 8.2 Hz, 1H), 7.63 (dd, J = 7.9, 1.2 Hz, 1H), (m, 3H), (m, 1H), 7.14 (t, J = 7.1 Hz, 1H), 6.92 (d, J = 8.6 Hz, 2H), 5.16 (s, 2H), 3.83 (s, 3H). 13 C NMR (101 MHz, cdcl 3 ) δ 159.4, 158.1, 153.9, 147.7, 137.6, 137.5, 130.0, 129.9, 128.9, 128.6, 122.9, 122.6, 121.7, 120.5, 113.8, 66.3, HRMS (EI) calcd. For C 20 H 18 N 2 O 3 [M]+ : Found: N-(2-(pyridin-2-yl)phenyl)acetamide(3y) chromatography on silica gel in 68% yield. 1 H NMR (400 MHz, CDCl 3 ) δ (s, 1H), 8.67 (d, J = 4.1 Hz, 1H), 8.54 (d, J = 8.1 Hz, 1H), 7.87 (td, J = 7.8, 1.8 Hz, 1H), 7.76 (d, J = 8.1 Hz, 1H), 7.66 (dd, J = 7.9, 1.4 Hz, 1H), (m, 1H), 7.31 (dd, J = 7.0, 5.4 Hz, 1H), 7.19 (t, J = 7.1 Hz, 1H), 2.20 (s, 3H). 13 C NMR (126 MHz, CDCl 3 ) δ 168.6, 158.3, 147.4, 137.7, 137.5, 130.0, 128.8, 125.6, 123.5, 123.1, 121.9, 121.9, HRMS (EI) calcd. For C 13 H 12 N 2 O[M]+ : Found: tert-butyl 2-(pyridin-2-yl)phenylcarbamate(3z) chromatography on silica gel in 60% yield. 1 H NMR (400 MHz, CDCl 3 ) δ (s, 1H), 8.68 (d, J = 4.0 Hz, 1H), 8.33 (d, J = 8.2 Hz, 1H), (m, 1H), 7.71 (d, J = 8.1 Hz, 1H), 7.61 (dd, J = 7.8, 1.5 Hz, 1H), 13
14 (m, 1H), (m, 1H), 7.11 (td, J = 7.8, 1.2 Hz, 1H), 1.54 (s, 9H). 13 C NMR (126 MHz, CDCl 3 ) δ 159.8, 154.8, 149.1, 139.5, 138.9, 131.3, 130.4, 126.9, 124.4, 123.6, 123.0, 121.8, 81.2, HRMS (EI) calcd. For C 16 H 18 N 2 O 2 [M]+ : Found: (9H-fluoren-9-yl)methyl 2-(pyridin-2-yl)phenylcarbamate(3aa) chromatography on silica gel in 55% yield. 1 H NMR (400 MHz, CDCl 3 ) δ (s, 1H), 8.76 (d, J = 4.2 Hz, 1H), 8.32 (s, 1H), 7.89 (td, J = 7.9, 1.8 Hz, 1H), 7.80 (dd, J = 7.8, 3.3 Hz, 3H), (m, 3H), 7.44 (m, 3H), (m, 3H), (m, 1H), 4.45 (d, J = 7.6 Hz, 2H), 4.35 (t, J = 7.5 Hz, 1H). 13 C NMR (101 MHz, CDCl 3 ) δ 158.2, 153.8, 147.4, 143.9, 141.3, 137.7, 137.6, 130.1, 128.7, 127.6, 127.0, 125.2, 122.9, 122.7, 121.8, 120.6, 119.9, 66.8, HRMS (EI) calcd. For C 26 H 20 N 2 O 2 [M]+ : Found: Mechanistic study: [Cp*Rh(MeCN) 3 ][SbF 6 ] 2 (2.5mol%), 2-Phenylpyridine (1) (0.1mmol) and D5-1 (0.1mmol), Acetohydroxamic acid (0.24mmol), silver carbonate (0.3mmol), THF (1ml) were added in a round-bottom flask. It was stirred at 100 for 2h, then 14
15 immediately quenched with EtOAc at the same time. The volatile was removed under reduced pressure and the crude product was purified by column chromatography on silica gel. Reference: S1: K. Fujita, Y. Takahashi, M. Owaki, K. Yamamoto, R. Yamaguchi, Org. Lett. 2004, 6, S2: Yang Li, Bi-Jie Li, Wen-Hua Wang, Wei-Ping Huang, Xi-Sha Zhang, Kang Chen, and Zhang-Jie Shi, Angew. Chem. Int. Ed. 2011, 50, S3: Donohoe, T.J., Chughtai, M.J., Klauber, D. J., Griffin, D., Cambell, A. D., J. Am. Chem. Soc. 2006, 128,
16 1 H and 13 C NMR Spectra of Compounds Compound 3a 16
17 Compound 3b 17
18 Compound 3c 18
19 Compound 3d 19
20 Compound 3e 20
21 Compound 3f 21
22 Compound 3g 22
23 Compound 3h 23
24 Compound 3i 24
25 Compound 3j 25
26 Compound 3k 26
27 Compound 3l 27
28 Compound 3m 28
29 Compound 3n 29
30 Compound 3o 30
31 Compound 3p 31
32 Compound 3q 32
33 Compound 3r 33
34 Compound 3s 34
35 Compound 3t 35
36 Compound 3u 36
37 Compound 3v 37
38 Compound 3w 38
39 Compound 3x 39
40 Compound 3y 40
41 Compound 3z 41
42 Compound 3aa 42
43 KIE experiment: 43
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