Auxiliary-Assisted Palladium-Catalyzed Arylation and Alkylation of sp2 and sp3 Carbon-Hydrogen Bonds
Dmitry Shabashov; Olafs Daugulis; Journal of the American Chemical Society 132 (2010) 3965–3972; doi:10.1021/ja910900p

data_4102147
_publ_section_title
;
 Auxiliary-Assisted Palladium-Catalyzed Arylation and Alkylation of sp2
 and sp3 Carbon-Hydrogen Bonds
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              3965
_journal_page_last               3972
_journal_paper_doi               10.1021/ja910900p
_journal_volume                  132
_journal_year                    2010
_chemical_formula_moiety         'C19 H23 Br2 N3 O Pd, C H2 Cl2'
_chemical_formula_sum            'C20 H25 Br2 Cl2 N3 O Pd'
_chemical_formula_weight         660.55
_chemical_name_systematic
; 
 ? 
;
_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                94.143(1)
_cell_angle_beta                 96.995(1)
_cell_angle_gamma                96.737(1)
_cell_formula_units_Z            2
_cell_length_a                   9.9480(9)
_cell_length_b                   10.5972(9)
_cell_length_c                   11.8562(10)
_cell_measurement_reflns_used    4193
_cell_measurement_temperature    223(2)
_cell_measurement_theta_max      25.07
_cell_measurement_theta_min      1.74
_cell_volume                     1227.27(18)
_computing_cell_refinement       'SAINT v7.12A (Bruker-Nonius, 2004)'
_computing_data_collection       'APEX2 v1.0-27 (Bruker-Nonius, 2005)'
_computing_data_reduction        'SAINT v7.12A (Bruker-Nonius, 2004)'
_computing_structure_refinement  'SHELXL v6.12 (G.M. Sheldrick, 2001)'
_computing_structure_solution    'SHELXS v6.12 (G.M. Sheldrick, 2001)'
_diffrn_ambient_temperature      223(2)
_diffrn_detector_area_resol_mean 4K
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_device_type  'Bruker-Nonius APEX II CCD'
_diffrn_measurement_method       CCD
_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    0.0151
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            6222
_diffrn_reflns_theta_full        25.07
_diffrn_reflns_theta_max         25.07
_diffrn_reflns_theta_min         1.74
_diffrn_standards_decay_%        0.0
_exptl_absorpt_coefficient_mu    4.246
_exptl_absorpt_correction_T_max  0.9901
_exptl_absorpt_correction_T_min  0.5997
_exptl_absorpt_correction_type   empirical
_exptl_crystal_colour            'Very dark green'
_exptl_crystal_density_diffrn    1.788
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             648
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.30
_refine_diff_density_max         2.231
_refine_diff_density_min         -0.691
_refine_diff_density_rms         0.084
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.008
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     262
_refine_ls_number_reflns         4279
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.008
_refine_ls_R_factor_all          0.0337
_refine_ls_R_factor_gt           0.0286
_refine_ls_shift/su_max          0.014
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0464P)^2^+2.0551P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0786
_refine_ls_wR_factor_ref         0.0822
_reflns_number_gt                3477
_reflns_number_total             4279
_reflns_threshold_expression     >4sigma(I)
_cod_data_source_file            ja910900p_si_002.cif
_cod_data_source_block           k1161
_cod_database_code               4102147