Intramolecular Palladium-Catalyzed Oxidative Amination of Furans: Synthesis of Functionalized Indoles.
Makarov, Anton S.; Uchuskin, Maxim G.; Gevorgyan, Vladimir; The Journal of organic chemistry 83 (2018) 14010–14021; doi:10.1021/acs.joc.8b02470

data_4034878
_publ_section_title
;
 Intramolecular Palladium-Catalyzed Oxidative Amination of Furans:
 Synthesis of Functionalized Indoles.
;
_journal_issue                   22
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              14010
_journal_page_last               14021
_journal_paper_doi               10.1021/acs.joc.8b02470
_journal_volume                  83
_journal_year                    2018
_chemical_formula_moiety         'C31 H24 Cl N O2 S'
_chemical_formula_sum            'C31 H24 Cl N O2 S'
_chemical_formula_weight         510.02
_chemical_name_systematic
2-((1E,3E)-4-(4-chlorophenyl)buta-1,3-dien-1-yl)-1-tosyl-1H-indole
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2017-02-16
_audit_creation_method
;
Olex2 1.2
(compiled 2017.01.04 svn.r3372 for OlexSys, GUI svn.r5292)
;
_audit_update_record
;
2018-04-19 deposited with the CCDC.
2018-08-03 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 104.739(18)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   19.084(4)
_cell_length_b                   7.0940(12)
_cell_length_c                   19.804(3)
_cell_measurement_reflns_used    2884
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      25.3160
_cell_measurement_theta_min      3.4690
_cell_volume                     2592.9(8)
_computing_cell_refinement
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
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_computing_data_collection
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_reduction
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_diffrn_ambient_temperature      295.15
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4752
_diffrn_detector_type            Ruby
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.861
_diffrn_measurement_details
;
  1 omega  -20.00    5.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -      -14.5541  -99.0000 -180.0000 25

  2 omega  -87.00   16.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -      -14.5541  -38.0000    0.0000 103

  3 omega  -23.00   64.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -      -14.5541   38.0000 -180.0000 87
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'New Xcalibur, Ruby'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0212495000
_diffrn_orient_matrix_UB_12      -0.0710443000
_diffrn_orient_matrix_UB_13      -0.0102134000
_diffrn_orient_matrix_UB_21      0.0319459000
_diffrn_orient_matrix_UB_22      0.0516728000
_diffrn_orient_matrix_UB_23      0.0152987000
_diffrn_orient_matrix_UB_31      0.0029068000
_diffrn_orient_matrix_UB_32      -0.0475324000
_diffrn_orient_matrix_UB_33      0.0321567000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0354
_diffrn_reflns_av_unetI/netI     0.0573
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.861
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            12920
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.861
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         29.364
_diffrn_reflns_theta_min         3.062
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.257
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.56394
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.306
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1064
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Petroleum ether - ethyl acetate'
_exptl_crystal_size_max          0.47
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.231
_refine_diff_density_min         -0.378
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.985
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     326
_refine_ls_number_reflns         6143
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.985
_refine_ls_R_factor_all          0.1040
_refine_ls_R_factor_gt           0.0542
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0688P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1293
_refine_ls_wR_factor_ref         0.1616
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3314
_reflns_number_total             6143
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b02470_si_002.cif
_cod_data_source_block           psu-471(am-900)
_cod_database_code               4034878
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'C H N S O Cl'
_reflns_odcompleteness_completeness 99.79
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C7(H7), C8(H8), C10(H10), C11(H11), C12(H12), C13(H13),
 C14(H14), C15(H15), C16(H16), C17(H17), C18(H18), C20(H20), C21(H21), C23(H23),
  C24(H24), C26(H26), C27(H27), C29(H29), C30(H30)
2.b Idealised Me refined as rotating group:
 C31(H31A,H31B,H31C)
;
_shelx_res_checksum              74747
_shelx_hkl_checksum              70156
_olex2_submission_special_instructions 'No special instructions were received'