Regioselective synthesis of multisubstituted benzenes by palladium-catalyzed intermolecular reaction of β-iodo-β-silylstyrenes with alkynes.
Kinoshita, Hidenori; Takahashi, Hirotoshi; Miura, Katsukiyo; Organic letters 15 (2013) 2962–2965; doi:10.1021/ol4010883

data_1556164
_publ_section_title
;
 Regioselective synthesis of multisubstituted benzenes by
 palladium-catalyzed intermolecular reaction of \b-iodo-\b-silylstyrenes
 with alkynes.
;
_journal_issue                   12
_journal_name_full               'Organic letters'
_journal_page_first              2962
_journal_page_last               2965
_journal_paper_doi               10.1021/ol4010883
_journal_volume                  15
_journal_year                    2013
_chemical_formula_moiety         'C36 H40 Si3'
_chemical_formula_sum            'C36 H40 Si3'
_chemical_formula_weight         556.95
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_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                98.9580(10)
_cell_angle_beta                 106.0780(10)
_cell_angle_gamma                97.7450(10)
_cell_formula_units_Z            2
_cell_length_a                   9.8245(6)
_cell_length_b                   10.2504(6)
_cell_length_c                   17.1303(11)
_cell_measurement_temperature    100(2)
_cell_volume                     1608.40(17)
_computing_cell_refinement       SMART
_computing_data_collection       'SMART (Bruker, 2000)'
_computing_data_reduction        'SAINT (Bruker, 2000)'
_computing_molecular_graphics    Ortep3
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'Sir 97'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.936
_diffrn_measured_fraction_theta_max 0.936
_diffrn_measurement_device_type  'Bruker Smart Apex II CCD diffractometer'
_diffrn_measurement_method       'phi and omega 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  0.0132
_diffrn_reflns_av_sigmaI/netI    0.0186
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            9160
_diffrn_reflns_theta_full        27.49
_diffrn_reflns_theta_max         27.49
_diffrn_reflns_theta_min         2.05
_exptl_absorpt_coefficient_mu    0.170
_exptl_absorpt_correction_T_max  0.9915
_exptl_absorpt_correction_T_min  0.9475
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   '(SADABS; Sheldrick 1996)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.150
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             596
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.355
_refine_diff_density_min         -0.262
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.357
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     358
_refine_ls_number_reflns         6929
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.357
_refine_ls_R_factor_all          0.0362
_refine_ls_R_factor_gt           0.0343
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1421
_refine_ls_wR_factor_ref         0.1497
_reflns_number_gt                6506
_reflns_number_total             6929
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol4010883_si_002.cif
_cod_data_source_block           takahash
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               1556164