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1 Electronic Supplementary Material (ESI) for RSC Advances. This journal is The Royal Society of Chemistry 27 Supporting Information Transition-metal-free PhI(Ac) 2 -promoted highly selective hydroboration of terminal alkynes under air Suyuan Chen, ab Lu Yang, ab Dong Yi, ab Qiang Fu, ab Zhijie Zhang, ab Wu Liang, ab Qiang Zhang,* a Jianxin Ji a and Wei Wei* c a Chengdu Institute of iology, Chinese Academy of Sciences, Chengdu 64, China. b University of the Chinese Academy of Sciences, eijing 49, China; c School of Chemistry and Chemical Engineering, Qufu Normal University, Qufu 27365, Shandong, China; weiweiqfnu@63.com (W. Wei); zhangqiang@cib.ac.cn (Q. Zhang) Contents. General information...s 2. Screening with different parameters...s 3. Typical experimental procedure...s3 4. Preliminary mechanistic studies...s3 5. Characterization data of products...s6 6. References...S 7. Copies of NMR spectra for products...s
2 . General information All chemicals and solvents were purchased from Aldrich, J&K and Alfa Aesar Chemical Company as reagent grade and used without further purification unless otherwise stated. H NMR, 3 C NMR and 9 F NMR were recorded on a ruker Avance 4 spectrometer at room temperature. H NMR, 3 C NMR and 9 F NMR spectra were collected in CDCl 3 (4 MHz H, MHz 3 C, 376 MHz 9 F) spectrometer with TMS as internal standard. Carbons with directly attached boron atoms were not observed, most likely due to quadrupolar relaxation. HRMS were performed on a rucker Daltonics io-tf-q mass spectrometer by the ESI method and LC-MS were obtained on a on a Waters Xevo TQ (Waters, Manchester, UK) equipped with an ESI source. The products were purified by flash column chromatography on silica gel (2-3 mesh). 2. Screening with different parameters Table S. ptimization of catalysts a + 2 pin 2 Cat. ase, solvent r.t., air, 2 h Pin a 2 3a Entry Catalyst ase Solvent Yield(%) b NaI t-una EtH 7 2 KI t-una EtH 8 3 TAI t-una EtH 3 4 PhI t-una EtH 7 5 KI 3 t-una EtH Hydroxy-,2- benziodoxole-3-one t-una EtH 2 7 PhI(Piv) 2 t-una EtH 25 8 PhI(TFA) 2 t-una EtH 36 9 Ph 2 IF 4 t-una EtH 8 PhI(Ac) 2 t-una EtH 9 Dess-Martin t-una EtH 2 a Reaction conditions: a (.5 mmol), 2 (.75 mmol), catalyst (5 mol%), t-una (2 equiv), EtH (4 ml), r.t., air, 2 h. b Isolated yields based on a. Table S2. ptimization of bases a. Entry Catalyst ase Solvent Yield(%) b PhI(Ac) 2 - EtH 2 PhI(Ac) 2 K 2 C 3 EtH 7 3 PhI(Ac) 2 Cs 2 C 3 EtH 6 4 PhI(Ac) 2 KH EtH 3 5 PhI(Ac) 2 LiH EtH 43 6 PhI(Ac) 2 DU EtH 7 7 PhI(Ac) 2 Et 3 N EtH 9 8 PhI(Ac) 2 DIPEA EtH n.d. S
3 9 PhI(Ac) 2 Pyridine EtH n.d. PhI(Ac) 2 DMAP EtH n.d. PhI(Ac) 2 MeNa EtH 5 2 PhI(Ac) 2 EtNa EtH 55 3 PhI(Ac) 2 t-uli EtH 5 4 PhI(Ac) 2 t-una EtH 9 5 PhI(Ac) 2 t-uk EtH 62 a Reaction conditions: a (.5 mmol), 2 (.75 mmol), PhI(Ac) 2 (5 mol%), base (2 equiv), EtH (4 ml), r.t., air, 2 h; DU:,5-diaza(5,4,)undec-5-ene; DIPEA: N,N -diisopropylethylamine; DMAP: 4-dimethylaminopyridine. b Isolated yields based on a. Table S3. ptimization of loading of catalyst a. Entry PhI(Ac) 2 ase Solvent Yield(%) b % t-una EtH % t-una EtH 42 3 % t-una EtH % t-una EtH % t-una EtH 9 6 8% t-una EtH % t-una EtH 9 a Reaction conditions: a (.5 mmol), 2 (.75 mmol), t-una (2 equiv), EtH (4 ml), r.t., air, 2 h. b Isolated yields based on a. Table S4. ptimization of solvents a. Entry Catalyst ase Solvent Yield(%) b PhI(Ac) 2 t-una MeH 4 2 PhI(Ac) 2 t-una EtH 9 3 PhI(Ac) 2 t-una n-prh 7 4 PhI(Ac) 2 t-una i-prh 55 5 PhI(Ac) 2 t-una t-uh 25 6 PhI(Ac) 2 t-una EtH 35 c a Reaction conditions: a (.5 mmol), 2 (.75 mmol), PhI(Ac) 2 (5 mol%), t- una (2 equiv), solvent (4 ml), r.t., air, 2 h. b Isolated yields based on a. c 95% EtH. Table S5. ptimization of loading of bases a. Entry Catalyst ase Solvent Yield(%) b PhI(Ac) 2.2 EtH 5 2 PhI(Ac) 2.5 EtH 39 3 PhI(Ac) 2. EtH 6 4 PhI(Ac) 2.3 EtH 69 5 PhI(Ac) 2.5 EtH 82 6 PhI(Ac) 2.8 EtH 9 7 PhI(Ac) 2 2. EtH 9 8 PhI(Ac) 2 EtH 9 a Reaction conditions: a (.5 mmol), 2 (.75 mmol), PhI(Ac) 2 (5 mol%), t- una, EtH (4 ml), r.t., air, 2 h. b Isolated yields based on a. S2
4 3. Typical experimental procedure α β PhI(Ac) 2 (5 mol%) β R + 2 pin 2 Pin t-una, EtH, air, r.t. R 2 3 Alkyne (.5 mmol), 2 Pin 2 2 (.75 mmol, 9 mg), t-una (.9 mmol, 87 mg), PhI(Ac) 2 (.75 mmol, 24 mg) were added to a round-bottom flask with EtH (4 ml). Then, the reaction mixture was stirred at room temperature under air for 2 h. After completion of the reaction, the reaction mixture was concentrated in vaccum. The residue was purified by flash chromatography on silica gel (petroleum ether / ethyl acetate) to afford the corresponding product Preliminary mechanistic studies () Radical trapping experiment + 2 pin 2 standard conditions TEMP ( equiv), N 2 Pin a 2 3a (89%) Phenylacetylene a (.5 mmol), 2 Pin 2 2 (.75 mmol, 9 mg), t-una (.9 mmol, 87 mg), TEMP (.5 mmol, 78 mg), and PhI(Ac) 2 (.75 mmol, 24 mg) were added to a round-bottom flask with EtH (4 ml), then the reaction mixture was stirred under at room temperature N 2 atmosphere for 2 h. The corresponding product 3a was still obtained in 89% yield. (2) LC-MS analysis 2 Pin 2 2 (.75 mmol, 9mg), PhI(Ac) 2 (.75 mmol, 24 mg), t-una (.9 mmol, 87 mg), - ethynyl-4-methoxybenzene b (.5 mmol), and EtH (4 ml) were added to a round-bottom flask equipped with a magnetic stirrer. Then, the reaction mixture was stirred at room temperature under air atmosphere for 4 h. This reaction mixture was directly analyzed by LC-MS. In addition to the desired product 3b, the [M+H] + ion peaks (m/z = 337.2, 39.) for intermediates A and E and the [M+Na] + ion peaks (m/z = 43.3, 545.) for intermediate C and D were detected. S3
5 (6.885) : MS2 ES e6 I % m/z Compound A (5.422) : MS2 ES e7 % 4 I m/z Compound C S4
6 (7.475) : MS2 ES e5 % I H Compound D m/z (2.68) : MS2 ES e6 % m/z Compound E I S5
7 (.7) : MS2 ES e6 % m/z Product 3b 5. Characterization data of products (3a-3t) (E)-4,4,5,5-tetramethyl-2-styryl-,3,2-dioxaborolane (3a) [2] : H NMR (4 MHz, CDCl 3 ) δ 2 (d, J = 8.3 Hz, 2H), 7.42 (d, J = 8.5 Hz, H), 7.35 (ddd, J = 2.3, 8.4, 4.2 Hz, 3H), 6.9 (d, J = 8.4 Hz, H),.34 (s, 2H). 3 C NMR ( MHz, CDCl 3 ) δ 49.53, 37.47, 28.92, 28.59, 27.8, 83.38, (E)-2-(4-methoxystyryl)-4,4,5,5-tetramethyl-,3,2-dioxaborolane (3b) [3] : H NMR (4 MHz, CDCl 3 ) δ 7.46 (d, J = 8.7 Hz, 2H), 7.38 (d, J = 8.4 Hz, H), 6.89 (d, J = 8.7 Hz, 2H), 6.4 (d, J = 8.4 Hz, H), 3.83 (s, 3H),.33 (s, 2H). 3 C NMR ( MHz, CDCl 3 ) δ 6.29, 49.8, 3.38, 28.47, 3.97, 83.22, 55.28, HR-MS(M+H) + calculated for C 5 H , found (E)-4,4,5,5-tetramethyl-2-(2-methylstyryl)-,3,2-dioxaborolane (3c) [2] : S6
8 H NMR (4 MHz, CDCl 3 ) δ 7.67 (d, J = 8.3 Hz, H), (m, H), 7.2 (dd, J = 6.2, 2.8 Hz, 2H), (m, H), 6. (d, J = 8.3 Hz, H), 2.45 (s, 3H),.34 (s, 2H). 3 C NMR ( MHz, CDCl 3 ) δ 47.4, 36.33, 34.75, 3.4, 28.59, 26.2, 25.78, 83.32, 24.84, HR-MS(M+H) + calculated for C 5 H , found (E)-4,4,5,5-tetramethyl-2-(3-methylstyryl)-,3,2-dioxaborolane (3d) [2] : H NMR (4 MHz, CDCl 3 ) δ 7.4 (d, J = 8.5 Hz, H), 7.32 (d, J = 5.7 Hz, 2H), 7.25 (t, J = 7.8 Hz, H), 7.4 (d, J = 7.4 Hz, H), 6.8 (d, J = 8.4 Hz, H), 2.37 (s, 3H),.34 (s, 2H). 3 C NMR ( MHz, CDCl 3 ) δ 49.7, 38.9, 37.48, 29.72, 28.47, 27.8, 24.26, 83.33, 24.82, 2.4. HR-MS(M+H) + calculated forc 5 H , found (E)-4,4,5,5-tetramethyl-2-(4-methylstyryl)-,3,2-dioxaborolane (3e) [3] : H NMR (4 MHz, CDCl 3 ) δ (m, 3H), 7.7 (d, J = 7.9 Hz, 2H), 6.3 (d, J = 8.4 Hz, H), 2.37 (s, 3H),.34 (s, 2H). 3 C NMR ( MHz, CDCl 3 ) δ 49.49, 38.99, 34.8, 29.3, 27.4, 83.3, 24.83, HR-MS(M+H) + calculated for C 5 H , found (E)-4,4,5,5-tetramethyl-2-(4-pentylstyryl)-,3,2-dioxaborolane (3f) [2] : n-u H NMR (4 MHz, CDCl 3 ) δ 7.43 (d, J = 8. Hz, 2H), 7.4 (d, J = 8.5 Hz, H), 7.7 (d, J = 8. Hz, 2H), 6.5 (d, J = 8.4 Hz, H), 2.6 (m, 2H),.63 (m, 2H),.34 (s, 6H),.9 (t, J = 6.9 Hz, 3H). 3 C NMR ( MHz, CDCl 3 ) δ 49.57, 44.6, 35.3, 28.65, 2, 83.28, 35.77,, 3., 24.82, 24, 4.3. HR- MS(M+H) + calculated for C 9 H , found (E)-2-(4-(tert-butyl)styryl)-4,4,5,5-tetramethyl-,3,2-dioxaborolane (3g) [4 ]: t-u S7
9 H NMR (4 MHz, CDCl3) δ 7.46 (d, J = 8.3 Hz, 2H), 7.4 (d, J = 8.4 Hz, H), 7.39 (d, J = 8.3 Hz, 3H), 6.5 (d, J = 8.4 Hz, H),.34 (s, 2H). 3 C NMR ( MHz, CDCl 3 ) δ 52.3, 49.4, 34.78, 26.84, 2, 83.29, 34.7, 3.25, HR-MS(M+H) + calculated for C 9 H , found (E)-3-(2-(4,4,5,5-tetramethyl-,3,2-dioxaborolan-2-yl)vinyl)aniline (3h) [3] : H 2 N H NMR (4 MHz, CDCl 3 ) H NMR (4 MHz, CDCl 3 ) δ 7.33 (d, J = 8.4 Hz, H), (t, J = 7.8 Hz, H), 6.92 (d, J = 7.6 Hz, H), 6.83 (s, H), (m, H), 6.2 (d, J = 8.4 Hz, H), 3.7 (s, 2H),.33 (s, 2H). 3 C NMR ( MHz, CDCl 3 ) δ 49.72, 46.45, 38.57, 29.46, 7.97, 5.93, 3.4, 83.32, HR- MS(M+H) + calculated for C 4 H 2 N , found (E)-2-(4-(2-(4,4,5,5-tetramethyl-,3,2-dioxaborolan-2-yl)vinyl)phenyl)acetonitrile (3i) [5] : NC H NMR (4 MHz, CDCl 3 ) δ (d, J = 8. Hz, 2H), 7.39 (d, J = 8.5 Hz, H), 7.3 (d, J = 8. Hz, 2H), 6.9 (d, J = 8.4 Hz, H), 3.76 (s, 2H),.33 (s, 2H). 3 C NMR ( MHz, CDCl 3 ) δ 48.32, 37.35, 32.82, 3.34, 28.2, 27.7, 7.69, 83.48, 24.83, HR-MS(M+H) + calculated for C 6 H 2 N , found (E)-2-(3-fluorostyryl)-4,4,5,5-tetramethyl-,3,2-dioxaborolane (3j) [2] : F H NMR (4 MHz, CDCl 3 ) δ 7.36 (d, J = 8.5 Hz, H), 7.32 (m, H), 7.26 (d, J = 7.7 Hz, H), (m, H), (m, H), 6.8 (d, J = 8.4 Hz, H),.34 (s, 2H). 3 C NMR ( MHz, CDCl 3 ) δ 63.7 (d, J = Hz), 48.7 (d, J = Hz), (d, J = Hz), 3.2 (d, J = 8.3 Hz), 23. (d, J = 2.7 Hz), 5.68 (d, J = Hz), 3.29 (d, J = Hz), 82, F NMR (376 MHz, CDCl 3 ) δ (E)-2-(2-chlorostyryl)-4,4,5,5-tetramethyl-,3,2-dioxaborolane (3k) [3] : Cl H NMR (4 MHz, CDCl 3 ) δ 7.8 (d, J = 8.4 Hz, H), 7.65 (dd, J = 7.3, 2. Hz, H), 7.37 (dd, J = 7.3,.8 Hz, H), (m, 2H), 6.9 (d, J = 8.3 Hz, H),.34 (s, 2H). 3 C NMR ( MHz, CDCl 3 ) δ 44.96, 38, 33.85, 29.79, 29.7, 27., 26.87, 8, HR-MS(M+H) + calculated for C 4 H 9 Cl , found (E)-4-(2-(4,4,5,5-tetramethyl-,3,2-dioxaborolan-2-yl)vinyl)benzonitrile (3l) [5] : S8
10 NC H NMR (4 MHz, CDCl 3 ) δ 7.64 (d, J = 8.2 Hz, 2H), 6 (d, J = 8.3 Hz, 2H), 7.38 (d, J = 8.4 Hz, H), 6.29 (d, J = 8.4 Hz, H),.33 (s, 2H). 3 C NMR ( MHz, CDCl 3 ) δ 47.2, 4.65, 32.45, 27.42, 8.8,.97, 83.74, HR-MS(M+Na) + calculated for C 5 H 8 NNa , found (E)--(4-(2-(4,4,5,5-tetramethyl-,3,2-dioxaborolan-2-yl)vinyl)phenyl)ethan--one (3m) [6] : H NMR (4 MHz, CDCl 3 ) δ 7.95 (d, J = 8.3 Hz, 2H), 7 (d, J = 8.3 Hz, 2H), 7.43 (d, J = 8.4 Hz, H), 6.3 (d, J = 8.4 Hz, H), 2.6 (s, 3H),.34 (s, 2H). 3 C NMR ( MHz, CDCl 3 ) δ 97.64, 48., 4.82, 36.98, 28.74, 27.2, 83.62, 26.7, (E)-2-(3-ethynylstyryl)-4,4,5,5-tetramethyl-,3,2-dioxaborolane (3n) [3] : H NMR (4 MHz, CDCl 3 ) δ 7.62 (s, H), 7.49 (d, J = 7.7 Hz, H), 7.44 (d, J = 7.7 Hz, H), 7.34 (m, 2H), 6.2 (d, J = 8.4 Hz, H), 3. (s, H),.34 (s, 2H). 3 C NMR ( MHz, CDCl 3 ) δ 48.3, 37.66, 32.37, 3.75, 28.6, 27.38, 22.43, 83.48, 83.37, 77.24, (E)-4,4,5,5-tetramethyl-2-(2-(naphthalen--yl)vinyl)-,3,2-dioxaborolane (3o) [7] : H NMR (4 MHz, CDCl 3 ) δ 8.29 (d, J = 8.3 Hz, H), 8.24 (d, J = 8.2 Hz, H), (m, 3H), 7.76 (d, J = 7.2 Hz, H), 3 (m, 4H), 6.29 (d, J = 8.2 Hz, H),.38 (s, 2H). 3 C NMR ( MHz, CDCl 3 ) δ 46.45, 35.37, 33.62, 3., 29.2, 28.49, 26.7, 25.79, 29, 24.8, 23.79, 83.43, (E)-4,4,5,5-tetramethyl-2-(2-(thiophen-3-yl)vinyl)-,3,2-dioxaborolane (3p) [2] : S H NMR (4 MHz, CDCl 3 ) δ 7.4 (d, J = 8.4 Hz, H), (m, 2H), 7.29 (dd, J = 4.7, 3. Hz, H), 5.97 (d, J = 8.4 Hz, H),.33 (s, 2H). 3 C NMR ( MHz, CDCl 3 ) δ 43.6, 4.22, 26.3, 25.3, 24.89, 83.33, S9
11 (E)-4,4,5,5-tetramethyl-2-(3-phenylprop--en--yl)-,3,2-dioxaborolane (3q) [3] : H NMR (4 MHz, CDCl 3 ) δ 7.3 (t, J = 7.4 Hz, 2H), 7.2 (dd, J = 2.7, 7.4 Hz, 3H), 6.79 (dt, J = 7.8, 6.3 Hz, H), 5.47 (d, J = 7.8 Hz, H), (d, J = 5.8 Hz, 2H),.28 (s, 2H). 3 C NMR ( MHz, CDCl 3 ) δ 52.47, 39.7, 28.94, 28.44, 26.5, 83.3, 42.29, HR-MS(M+H) + calculated for C 5 H , found (E)-2-(3,3-dimethylbut--en--yl)-4,4,5,5-tetramethyl-,3,2-dioxaborolane (3r) [8] : H NMR (4 MHz, CDCl 3 ) δ 6.63 (d, J = 8.3 Hz, H), 5.34 (d, J = 8.3 Hz, H),.27 (s, 3H),. (s, 9H). 3 C NMR ( MHz, CDCl 3 ) δ 64.36, 82.95, 34.98, 28.78, HR-MS(M+Na) + calculated for C 2 H 23 Na , found (E)-2-(3-cyclopentylprop--en--yl)-4,4,5,5-tetramethyl-,3,2-dioxaborolane (3s) [9] : H NMR (4 MHz, CDCl 3 ) δ 6.64 (dt, J = 7.8, 6.7 Hz, H), 5.43 (d, J = 7.9 Hz, H), 2.8 (t, J = 6.9 Hz, 2H),.92 (dt, J = 5., 7.6 Hz, H),.77 (dt, J =.3, 6.8 Hz, 2H), (m, 4H),.29 (s, 2H),.4 (dt, J = 9.2, 7.2 Hz, 2H). 3 C NMR ( MHz, CDCl 3 ) δ 54.2, 82.98, 42.48, 39., 32.42, 25.7, HR- MS(M+Na) + calculated for C 4 H 25 Na , found (E)-2-(2-cyclopropylvinyl)-4,4,5,5-tetramethyl-,3,2-dioxaborolane (3t) [2] : H NMR (4 MHz, CDCl 3 ) δ 6. (dd, J = 7.8, 9.3 Hz, H), 2 (d, J = 7.8 Hz, H),.56.5 (m, H),.28 (s, 2H),.83 (dt, J = 6.3, 4.3 Hz, 2H),.6.53 (m, 2H). 3 C NMR ( MHz, CDCl 3 ) δ 58.58, 82.93, 24.76, 7.2, References []. Wrackmeyer, Prog. Nucl. Magn. Reson. Spectrosc., 979, 2, [2] J. Zhao, Z. Niu, H. Fu and Y. Li, Chem. Commun., 24, 5, [3] S. Hong, W. Zhang, M. Liu, Z.-J. Yao and W. Deng, Tetrahedron Lett., 26, 57, -4. [4] M. Fleige, J. Möbus, T. vom Stein, F. Glorius and D. W. Stephan, Chem. Commun., 26, 52, [5] C. Feng, H. Wang, L. Xu and P. Li, rg. iomol. Chem., 25, 3, [6] M. Murata, S. Watanabe and Y. Masuda, Journal of Chemical Research, 22, 22, [7] Y.-W. Zhao, Q. Feng and Q.-L. Song, Chin. Chem. Lett., 26, 27, S
12 [8] A. ismuto, S. P. Thomas and M. J. Cowley, Angew. Chem. Int. Ed., 26, 55, [9] H. Jang, A. R. Zhugralin, Y. Lee and A. H. Hoveyda, J. Am. Chem. Soc., 2, 33, S
13 S2 7. Copies of NMR spectra for products 3a
14 S3 3b
15 S4 3c
16 S5 3d
17 S6 3e
18 S7 3f
19 S8 3g
20 S9 3h H 2 N H 2 N
21 S2 3i N N
22 S2 3j F F
23 S22 3k Cl Cl
24 S23 3l N N
25 S24 3m
26 S25 3n
27 S26 3o
28 S27 3p S S
29 S28 3q
30 S29 3r
31 S3 3s
32 3t S3
33 S32 3s β:α=82:8 3t β:α=93:7
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