Palladium-Catalyzed Conjugate Addition to Electron-Deficient Alkynes with Benzenesulfinic Acid Derived from 1,2-Bis(phenylsulfonyl)ethane: Selective Synthesis of (E)-Vinyl Sulfones
Ren-Jie Song; Yu Liu; Yan-Yun Liu; Jin-Heng Li; Journal of Organic Chemistry 76 (2011) 1001–1004; doi:10.1021/jo102359n

data_4026038
_publ_section_title
;
 Palladium-Catalyzed Conjugate Addition to Electron-Deficient Alkynes with
 Benzenesulfinic Acid Derived from 1,2-Bis(phenylsulfonyl)ethane:
 Selective Synthesis of (E)-Vinyl Sulfones
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              1001
_journal_page_last               1004
_journal_paper_doi               10.1021/jo102359n
_journal_volume                  76
_journal_year                    2011
_chemical_formula_moiety         'C28 H23 N O3 S'
_chemical_formula_sum            'C28 H23 N O3 S'
_chemical_formula_weight         453.53
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 91.566(8)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.574(4)
_cell_length_b                   17.640(7)
_cell_length_c                   12.926(5)
_cell_measurement_reflns_used    2267
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      21.086
_cell_measurement_theta_min      2.229
_cell_volume                     2410.1(16)
_computing_cell_refinement       'SAINT (Bruker, 2002)'
_computing_data_collection       'SMART (Bruker, 2002)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'SHELXTL(Bruker, 2002)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX area-detector diffractometer'
_diffrn_measurement_method       '\f and \w scan'
_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  0.0326
_diffrn_reflns_av_sigmaI/netI    0.0405
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            12521
_diffrn_reflns_theta_full        25.02
_diffrn_reflns_theta_max         25.02
_diffrn_reflns_theta_min         1.95
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.164
_exptl_absorpt_correction_T_max  0.9618
_exptl_absorpt_correction_T_min  0.9227
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2002)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.250
_exptl_crystal_description       block
_exptl_crystal_F_000             952
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.24
_refine_diff_density_max         0.443
_refine_diff_density_min         -0.201
_refine_diff_density_rms         0.047
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.333
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     298
_refine_ls_number_reflns         4257
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.333
_refine_ls_R_factor_all          0.1273
_refine_ls_R_factor_gt           0.1114
_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^)+(0.0683P)^2^+1.7969P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2208
_refine_ls_wR_factor_ref         0.2286
_reflns_number_gt                3633
_reflns_number_total             4257
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            jo102359n_si_001.cif
_cod_data_source_block           1143m
_cod_original_cell_volume        2410.1(17)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4026038