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_4102558
_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_moiety         'C18 H19 Br O2'
_chemical_formula_sum            'C18 H19 Br O2'
_chemical_formula_weight         347.24
_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                 107.7090(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.8824(12)
_cell_length_b                   7.9467(7)
_cell_length_c                   16.7333(16)
_cell_measurement_reflns_used    9972
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      26.41
_cell_measurement_theta_min      2.38
_cell_volume                     1631.9(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, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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  0.0242
_diffrn_reflns_av_sigmaI/netI    0.0151
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            33141
_diffrn_reflns_theta_full        28.36
_diffrn_reflns_theta_max         28.36
_diffrn_reflns_theta_min         2.38
_exptl_absorpt_coefficient_mu    2.521
_exptl_absorpt_correction_T_max  0.8143
_exptl_absorpt_correction_T_min  0.4321
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
  Blessing, R. Acta Cryst. (1995) A51 33-38.
  Sheldrick, G.  SADABS (Version 2008/1) Bruker AXS area
  detector absorption and other corrections, University of
  Gottingen, Germany 2008.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.413
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             712
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.663
_refine_diff_density_min         -0.543
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.011
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         4073
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.011
_refine_ls_R_factor_all          0.0405
_refine_ls_R_factor_gt           0.0300
_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^)+(0.0345P)^2^+0.7360P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0726
_refine_ls_wR_factor_ref         0.0784
_reflns_number_gt                3316
_reflns_number_total             4073
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja101851v_si_001.cif
_cod_data_source_block           dk222
_cod_database_code               4102558