PPh 3.HBr-DMSO: A Reagent System for Diverse Chemoselective Transformations
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1 Supporting Information PPh 3.HBr-DMS: A Reagent System for Diverse Chemoselective Transformations Kanchan Mal, Amanpreet Kaur, Fazle Haque, and Indrajit Das* ( These authors contributed equally) Chemistry Division, CSIR-Indian Institute of Chemical Biology Kolkata , India id@csiriicb.in Table of Contents: 1. NMR ( 1 H, 13 C, DEPT-135) Spectra S2-S98 2. RTEP Diagram..S98-S100 S1
2 H, 13 C, and DEPT-135 NMR Spectra 1 H, 13 C, DEPT-135 NMR spectra of 2a: AK-93A-C r_13c.esp Tf S2
3 H, 13 C, DEPT-135 NMR spectra of 2b: ID r_ID H.esp H S3
4 ID r_ID C.esp H ID r_ID DEPT.esp H S4
5 1 H, 13 C, DEPT-135 NMR spectra of 2c: ID R_ID-874-1H.ESP Me ID R_ID C.ESP Me S5
6 ID R_ID-874-DEPT.ESP Me H, 13 C, DEPT-135 NMR spectra of 2d: ID R_ID H.ESP Me S6
7 ID R_ID C.ESP Me ID R_ID-4912-DEPT.ESP Me S7
8 1 H, 13 C, DEPT-135 NMR spectra of 2e: ID R_ID H.ESP Me ID R_ID C.ESP Me S8
9 ID R_ID-4911-DEPT.ESP Me H, 13 C, DEPT-135 NMR spectra of 2f: ID R_AK H.ESP S9
10 ID R_AK C.ESP ID R_AK-1211-DEPT.ESP S10
11 H, 13 C, DEPT-135 NMR spectra of 2g: ID-40A-1H.001_1H.esp Br ID C r_13C.esp Br S11
12 ID C r_DEPT-135.esp Br H, 13 C, DEPT-135 NMR spectra of 2ga: S12
13 S13
14 H, 13 C, DEPT-135 NMR spectra of 2h: AK H R_AK H.ESP S Cl ID-2031-C r_13C_300.esp Cl S S14
15 ID-2031-C r_DEPT-135.esp Cl S 1 H, 13 C, DEPT-135 NMR spectra of 2i: ID-103-T-1H r_1H.esp S Br S15
16 ID-103-T-C r_13c.esp S Br ID-103-T-C r_DEPT.esp S Br S16
17 H, 13 C, DEPT-135 NMR spectra of 4a: ID R_ID-362-1H.ESP H Cl Me S Me Me ID R_ID C.ESP H Cl Me S Me Me S17
18 ID R_ID-362-DEPT-135.ESP H Cl Me S Me Me H, 13 C, DEPT-135 NMR spectra of 4b: S18
19 S19
20 H, 13 C, DEPT-135 NMR spectra of 5b: ID r_ID-367-B-1H.esp Cl S ID r_ID-367-B-13C.esp Cl S S20
21 ID r_ID-367-B_DEPT.esp Cl S H, 13 C, DEPT-135 NMR spectra of 4c: S21
22 S22
23 H, 13 C, DEPT-135 NMR spectra of 5c: ID R_ID-383-1H.ESP S S23
24 ID r_ID C.esp S ID r_ID-383-DEPT-135.esp S S24
25 1 H, 13 C, DEPT-135 NMR spectra of 4d: S25
26 H, 13 C, DEPT-135 NMR spectra of 5d: ID r_ID-330-1H.esp Me S S26
27 ID r_ID C.esp Me S ID r_ID-330-DEPT-135.esp Me S S27
28 1 H, 13 C, DEPT-135 NMR spectra of 4e: S28
29 H, 13 C, DEPT-135 NMR spectra of 5e: ID r_ID Cl-1H.esp Cl S S29
30 ID r_ID CL-13C.esp Cl S ID r_ID CL-DEPT-135.esp Cl S S30
31 H, 13 C, DEPT-135 NMR spectra of 4f: ID-314-F-1H.esp H F S ID r_ID-314-F-13C.esp H F S S31
32 ID r_ID-314-F-DEPT-135.esp H F S H, 13 C, DEPT-135 NMR spectra of 5f: ID r_ID F-1H.esp F S S32
33 ID r_ID F-13C.esp F S ID r_ID F-DEPT-135.esp F S S33
34 1 H, 13 C, DEPT-135 NMR spectra of 4g: S34
35 1 H, 13 C, DEPT-135 NMR spectra of 5g: S35
36 S36
37 1 H, 13 C, DEPT-135 NMR spectra of 4h: S37
38 1 H, 13 C, DEPT-135 NMR spectra of 5h: S38
39 S39
40 H, 13 C, DEPT-135 NMR spectra of 4i: ID r_KM-60-UP-1H.esp S H ID r_KM-60-UP-13C.esp S H S40
41 ID r_KM-60-UP-DEPT.esp S H 1 H, 13 C, DEPT-135 NMR spectra of 5i: ID R_ID-303-UP-1H.ESP S S41
42 ID R_ID-303-UP-13C.ESP S ID R_ID-303-UP-DEPT-135.ESP S S42
43 1 H, 13 C, DEPT-135 NMR spectra of 4j: S43
44 1 H, 13 C, DEPT-135 NMR spectra of 4k: S44
45 S45
46 H, 13 C, DEPT-135 NMR spectra of 5k: ID R_KM-353-UP-1H.ESP ID R_KM-353-UP-13C.ESP S46
47 ID R_KM-353-UP-DEPT.ESP H, 13 C, DEPT-135 NMR spectra of 4l: ID R_AK-4-1H.ESP Br H S47
48 ID R_AK-4-13C.ESP Br H ID R_AK-4-DEPT.ESP Br H S48
49 1 H, 13 C, DEPT-135 NMR spectra of 4m: S49
50 H, 13 C, DEPT-135 NMR spectra of 5m: ID r_ID DMe-UP-1H.esp Me Me S50
51 ID r_ID DME-UP-13C.esp Me Me ID r_ID DMe-Up-DEPt-135.esp Me Me S51
52 H, 13 C, DEPT-135 NMR spectra of 4n: ID r.esp H Me S52
53 ID r_ID-355-L-DEPT.esp H Me 1 H, 13 C, DEPT-135 NMR spectra of 5n: ID _ID-204-P-ME-1H.ESP Me S53
54 ID R_ID-204-P-ME-1H.ESP Me ID R_ID-204-P-ME-DEPT.ESP Me S54
55 H, 13 C, DEPT-135 NMR spectra of 4o: ID R_AK-8-1H.ESP H F ID R_AK-8-13C.ESP H F S55
56 ID R_AK-8-DEPT.ESP H F 1 H, 13 C, DEPT-135 NMR spectra of 5o: ID _ID F-1H.ESP F S56
57 ID R_ID F-13C.ESP F ID R_ID F-DEPT.ESP F S57
58 H, 13 C, DEPT-135 NMR spectra of 4p: ID R_ID-304-L-1H.ESP H CH ID R_ID-304-L-13C.ESP H CH 3 S58
59 ID R_ID-304-L-DEPT-135.ESP H CH 3 1 H, 13 C, DEPT-135 NMR spectra of 5p: ID r_ID-304-1H.esp S59
60 ID r_ID C.esp ID r_ID-304-DEPT-135.esp S60
61 1 H and 13 C NMR spectra of 4q: S61
62 H, 13 C, DEPT-135 NMR spectra of 4r: ID-8515-C R_ID C.ESP Me H Me 220 S62
63 ID-8515-C R_ID-8515-DEPT.ESP Me H Me H and 13 C NMR spectra of 4s: S63
64 1 H, 13 C, DEPT-135 NMR spectra of 4t: S64
65 S65
66 1 H, 13 C, DEPT-135 NMR spectra of 4u: S66
67 S67
68 1 H and 13 C NMR spectra of 7a: S68
69 H, 13 C, DEPT-135 NMR spectra of 7b: ID R_ID-67-MD-1H.esp Me ID R_ID-67-MD-13C.ESP Me S69
70 ID R_ID-67-MD-DEPT.ESP Me 1 H, 13 C, DEPT-135 NMR spectra of 7c: ID R_ID-73-B-1H.ESP Me S70
71 ID R_ID-73-B-13C.ESP Me ID R_ID-73-B-DEPT.ESP Me S71
72 H, 13 C, DEPT-135 NMR spectra of 7d: ID R_ID-83-A-1H.ESP Me Br Me ID R_ID-83-A-13C.ESP Me Br Me S72
73 ID R_ID-83-A-DEPT-135.ESP Me Br Me 1 H, 13 C, DEPT-135 NMR spectra of 7e: ID R_ID-80-B-1H.ESP Br S73
74 ID R_ID-80-B-13C.ESP Br ID R_ID-80B-DEPT.ESP Br S74
75 H, 13 C, DEPT-135 NMR spectra of 9a: ID R_ID-75-A-1H.ESP Ph Br ID R_ID-75-A-13C.ESP Br Ph S75
76 ID R_ID-75-A-DEPT-135.ESP Ph Br H and 13 C NMR spectra of 9b: S76
77 H, 13 C, DEPT-135 NMR spectra of 10a: ID r_ID-114-5BR-MD.esp Br SMe S77
78 ID r_ID-114-5BR-MD-13C.esp Br SMe ID r_ID-114-5BR-MD-DEPT-135.esp Br SMe S78
79 H, 13 C, DEPT-135 NMR spectra of 10aa: ID r_ID-114-5BR-UP.esp Br Br Br ID r_ID-114-5BR-UP-13C.esp Br Br Br S79
80 ID r_ID-114-5BR-UP-DEPT-135.esp Br Br Br H, 13 C, DEPT-135 NMR spectra of 10ab: ID r_ID-114-5BR-L-1H.esp Br Br S80
81 ID r_ID-114-5BR-L-13C.esp Br Br ID r_ID-114-5BR-L-DEPT-135.esp Br Br S81
82 H, 13 C, DEPT-135 NMR spectra of 10b: ID r_ID-102-ME-MD-1H.esp Me SMe ID r_ID-102-ME-MD-13C.esp Me SMe S82
83 ID r_ID-102-ME-MD-DEPT-135.esp Me SMe H, 13 C, DEPT-135 NMR spectra of 10ba: ID r_ID-102-Me-UP-1H.esp Me Br Br S83
84 ID r_ID-102-Me-UP-13C.esp Me Br Br ID r_ID-102-Me-Up-DEPT-135.esp Me Br Br S84
85 H, 13 C, DEPT-135 NMR spectra of 10bb: ID r_ID-102-Me-Lo-1H.esp Me Br ID r_ID-102-Me-Lo-13C.esp Me Br S85
86 ID r_ID-102-Me-Lo-DEPT-135.esp Me Br H, 13 C, DEPT-135 NMR spectra of 12a: ID r_AS-119-Et-1H.esp S86
87 ID R_AS-119-ET-13C.ESP ID r_As-119-Et-DEPT-135.esp S87
88 H, 13 C, DEPT-135 NMR spectra of 12b: ID R_AS-128-ET-1H.ESP Me ID r_As-128-Et-1H.esp Me 220 S88
89 ID r_AS-128-Et-DEPT-135.esp Me H, 13 C, DEPT-135 NMR spectra of 14: ID r_ID-337-1H.esp S89
90 ID r_ID C.esp ID r_ID-337-DEPT-135.esp S90
91 H, 13 C, DEPT-135 NMR spectra of 14a: ID r_ID-346-1H.esp H ID r_ID C.esp H S91
92 ID r_ID-346-DEPT-135.esp H 1 H, 13 C, DEPT-135 NMR spectra of 16: ID r_AS-120-IP-1H.esp Br S92
93 S93
94 1 H, 13 C, DEPT-135 NMR spectra of 17a: ID R_ID-110-S-1H.ESP ID R_ID-110-S-13C.ESP Ph Ph S94
95 ID R_ID-110-S-DEPT-135.ESP Ph Ph 1 H, 13 C, DEPT-135 NMR spectra of 17b: S95
96 S96
97 1 H, 13 C, DEPT-135 NMR spectra of 18: S97
98 Crystal Structure: Single crystals were grown by slow evaporation of the compounds from dichloromethane/acetone solvents. Data were collected at 293K on a Bruker Kappa APEX2 CCD diffractometer equipped graphite monochromated and MonoCap-collimated with MoKα radiation. 1 Preliminary lattice parameters and orientation matrices were obtained from three sets of frames. Then full data were collected using the ω and ɸ scan method with the frame width of 0.5. Data were processed with the SAINT+ program for reduction and cell refinement. 2 Multiscan absorption corrections were applied by using the SADABS program for area detector. 3 All structures were solved with SHELXT 4 and refined with SHELXL 5 using lex2 program APEXII, Program for Bruker CCD X-ray Diffractometer Control; Bruker AXS, Inc.: Madison, WI, SAINT+, Program for reduction of data collected on a Bruker CCD area detector diffractometer; Bruker AXS, Inc.:Madison, WI, Sheldric. M. S S rogram for em irical absor tion correction of areadetector data ni ersit t ttingen ttingen, Germany, Sheldrick, G. M. Acta Cryst., 2015, A71, Sheldrick, G. M. Acta Cryst. 2015, C71, Dolomanov,. V.; Bourhis, L. J.; Gildea, R. J.; Howard, J. A. K.; Puschmann, H. J. Appl. Cryst. 2009, 42, S98
99 Figure S1: X-ray determined molecular structure of 10a. The thermal ellipsoids are shown in 50% probability level. Datablock: 10a Bond precision: C-C = A Wavelength= Cell: a=4.0495(13) b=5.6747(18) c=41.897(13) alpha=90 beta=91.009(5) gamma=90 Temperature: 296 K Calculated Reported Volume 962.6(5) 962.6(5) Space group P 21/n P 1 21/n 1 Hall group -P 2yn -P 2yn Moiety formula C10 H7 Br S C10 H7 Br S Sum formula C10 H7 Br S C10 H7 Br S Mr Dx,g cm Z 4 4 Mu (mm-1) F F000' h,k,lmax 4,6,50 4,6,49 Nref Tmin,Tmax 0.234, ,0.745 Tmin' Correction method= MULTI-SCAN Data completeness= Theta(max)= R(reflections)= ( 1334) wr2(reflections)= ( 1547) S = Npar= 119 Alert level A PLAT029_ALERT_3_A _diffrn_measured_fraction_theta_full Low Note Reason: The crystal thickness is very thin. S99
100 Table 1. Fractional Atomic Coordinates ( 10 4 ) and Equivalent Isotropic Displacement Parameters (Å ) for 10a. U eq is defined as 1/3 of of the trace of the orthogonalised U IJ tensor. Atom x y z U(eq) Br (13) 592.0(9) (2) 51.6(2) C1 7540(11) 5081(7) (11) 36.4(10) C2 7911(12) 5896(7) (11) 45.1(11) C3 6686(13) 4563(7) (12) 47.2(12) C4 5116(10) 2466(7) (10) 38.1(10) C5 4639(11) 1614(7) (10) 38.6(10) C6 5901(10) 2966(7) (9) 34.2(9) C7 5879(11) 2556(7) (10) 40.1(10) C8 7479(11) 4331(7) (10) 40.6(10) C9 8677(11) 6063(7) (11) 40.7(10) C (15) 2171(9) (12) 64.9(15) (9) 7836(5) (8) 60.0(9) S1 8369(4) 4838(2) (3) 54.7(4) S100
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