KIO3-Catalyzed Aerobic Cross-Coupling Reactions of Enaminones and Thiophenols: Synthesis of Polyfunctionalized Alkenes by Metal-Free C-H Sulfenylation.
Wan, Jie-Ping; Zhong, Shanshan; Xie, Lili; Cao, Xiaoji; Liu, Yunyun; Wei, Li; Organic letters 18 (2016) 584–587; doi:10.1021/acs.orglett.5b03608

data_1542317
_publ_section_title
;
 KIO3-Catalyzed Aerobic Cross-Coupling Reactions of Enaminones and
 Thiophenols: Synthesis of Polyfunctionalized Alkenes by Metal-Free C-H
 Sulfenylation.
;
_journal_issue                   3
_journal_name_full               'Organic letters'
_journal_page_first              584
_journal_page_last               587
_journal_paper_doi               10.1021/acs.orglett.5b03608
_journal_volume                  18
_journal_year                    2016
_chemical_formula_moiety         'C18 H18 Cl N O S'
_chemical_formula_sum            'C18 H18 Cl N O S'
_chemical_formula_weight         331.84
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                78.52(3)
_cell_angle_beta                 85.68(3)
_cell_angle_gamma                79.53(3)
_cell_formula_units_Z            2
_cell_length_a                   6.3258(13)
_cell_length_b                   8.2673(17)
_cell_length_c                   16.726(3)
_cell_measurement_reflns_used    5334
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      3.0
_cell_volume                     842.3(3)
_computing_cell_refinement       RAPID-AUTO
_computing_data_collection       'RAPID-AUTO (Rigaku, 1998)'
_computing_data_reduction        'CrystalStructure (Rigaku/MSC, 2004)'
_computing_molecular_graphics    'ORTEPII (Johnson, 1976)'
_computing_publication_material  SHELXL-97
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      295(2)
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0332
_diffrn_reflns_av_sigmaI/netI    0.0385
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            6794
_diffrn_reflns_theta_full        25.35
_diffrn_reflns_theta_max         25.35
_diffrn_reflns_theta_min         3.04
_diffrn_standards_decay_%        0
_diffrn_standards_number         image
_exptl_absorpt_coefficient_mu    0.352
_exptl_absorpt_correction_T_max  0.826
_exptl_absorpt_correction_T_min  0.745
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Higashi, 1995)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.308
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             348
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.26
_refine_diff_density_max         0.308
_refine_diff_density_min         -0.331
_refine_diff_density_rms         0.056
_refine_ls_extinction_coef       0.040(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.161
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         3058
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.161
_refine_ls_R_factor_all          0.0745
_refine_ls_R_factor_gt           0.0470
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0659P)^2^+0.3473P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1233
_refine_ls_wR_factor_ref         0.1642
_reflns_number_gt                2072
_reflns_number_total             3058
_reflns_threshold_expression     >2\s(I)
_cod_data_source_file            ol5b03608_si_002.cif
_cod_data_source_block           shx97
_cod_depositor_comments          'Adding full bibliography for 1542317.cif.'
_cod_database_code               1542317