Palladium-Catalyzed Bisolefination of C-C Triple Bonds: A Facile Method for the Synthesis of Naphthalene Derivatives
Chao Feng; Teck-Peng Loh; Journal of the American Chemical Society 132 (2010) 17710–17712; doi:10.1021/ja108998d

data_4103706
_publ_section_title
;
 Palladium-Catalyzed Bisolefination of C-C Triple Bonds: A Facile Method
 for the Synthesis of Naphthalene Derivatives
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              17710
_journal_page_last               17712
_journal_paper_doi               10.1021/ja108998d
_journal_volume                  132
_journal_year                    2010
_chemical_formula_moiety         'C27 H20 N2 O6, C H2 Cl2'
_chemical_formula_sum            'C28 H22 Cl2 N2 O6'
_chemical_formula_weight         553.38
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 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                 111.0420(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.91460(10)
_cell_length_b                   24.6124(4)
_cell_length_c                   16.4864(2)
_cell_measurement_reflns_used    9894
_cell_measurement_temperature    103(2)
_cell_measurement_theta_max      36.16
_cell_measurement_theta_min      2.65
_cell_volume                     2618.64(7)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      103(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \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  0.0394
_diffrn_reflns_av_sigmaI/netI    0.0305
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       41
_diffrn_reflns_limit_k_min       -41
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            73665
_diffrn_reflns_theta_full        36.49
_diffrn_reflns_theta_max         36.49
_diffrn_reflns_theta_min         1.56
_exptl_absorpt_coefficient_mu    0.294
_exptl_absorpt_correction_T_max  0.9712
_exptl_absorpt_correction_T_min  0.8914
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.404
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1144
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         2.459
_refine_diff_density_min         -1.453
_refine_diff_density_rms         0.131
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     372
_refine_ls_number_reflns         12757
_refine_ls_number_restraints     54
_refine_ls_restrained_S_all      1.055
_refine_ls_R_factor_all          0.1265
_refine_ls_R_factor_gt           0.0931
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1811P)^2^+3.2836P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2787
_refine_ls_wR_factor_ref         0.3216
_reflns_number_gt                8795
_reflns_number_total             12757
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja108998d_si_002.cif
_cod_data_source_block           ltp127s
_cod_database_code               4103706