Palladium-Catalyzed Oxidative Arylhalogenation of Alkenes: Synthetic Scope and Mechanistic Insights
Dipannita Kalyani; Andrew D. Satterfield; Melanie S. Sanford; Journal of the American Chemical Society 132 (2010) 8419–8427; doi:10.1021/ja101851v

data_4102559
_publ_section_title
;
 Palladium-Catalyzed Oxidative Arylhalogenation of Alkenes: Synthetic
 Scope and Mechanistic Insights
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              8419
_journal_page_last               8427
_journal_paper_doi               10.1021/ja101851v
_journal_volume                  132
_journal_year                    2010
_chemical_formula_sum            'C29 H25 Cl O2'
_chemical_formula_weight         440.94
_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                102.594(1)
_cell_angle_beta                 99.673(1)
_cell_angle_gamma                103.003(1)
_cell_formula_units_Z            4
_cell_length_a                   10.4220(7)
_cell_length_b                   14.4036(9)
_cell_length_c                   16.715(1)
_cell_measurement_reflns_used    9856
_cell_measurement_temperature    180(2)
_cell_measurement_theta_max      27.27
_cell_measurement_theta_min      2.22
_cell_volume                     2323.0(3)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker SMART-APEX'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      180(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'CCD area detector'
_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  0.0454
_diffrn_reflns_av_sigmaI/netI    0.0298
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            77825
_diffrn_reflns_theta_full        27.37
_diffrn_reflns_theta_max         27.37
_diffrn_reflns_theta_min         1.51
_exptl_absorpt_coefficient_mu    0.188
_exptl_absorpt_correction_T_max  0.9851
_exptl_absorpt_correction_T_min  0.9669
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
  Blessing, R. Acta Cryst. (1995) A51 33-38.
  Sheldrick, G.  SADABS (Version 2007/4) Bruker AXS area
  detector absorption and other corrections, University of 
  Gottingen, Germany 2007.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.261
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             928
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.306
_refine_diff_density_min         -0.276
_refine_diff_density_rms         0.039
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.010
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     577
_refine_ls_number_reflns         10525
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.010
_refine_ls_R_factor_all          0.0657
_refine_ls_R_factor_gt           0.0417
_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^)+(0.0566P)^2^+0.4331P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1013
_refine_ls_wR_factor_ref         0.1141
_reflns_number_gt                7708
_reflns_number_total             10525
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja101851v_si_002.cif
_cod_data_source_block           dk283
_cod_database_code               4102559