Pd-catalyzed nucleophilic fluorination of aryl bromides.
Lee, Hong Geun; Milner, Phillip J.; Buchwald, Stephen L.; Journal of the American Chemical Society 136 (2014) 3792–3795; doi:10.1021/ja5009739

data_4121450
_publ_section_title
;
 Pd-catalyzed nucleophilic fluorination of aryl bromides.
;
_journal_issue                   10
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              3792
_journal_page_last               3795
_journal_paper_doi               10.1021/ja5009739
_journal_volume                  136
_journal_year                    2014
_chemical_formula_sum            'C53 H73 O2 P'
_chemical_formula_weight         773.08
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_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-2012
_cell_angle_alpha                89.3210(10)
_cell_angle_beta                 71.7150(10)
_cell_angle_gamma                69.4330(10)
_cell_formula_units_Z            4
_cell_length_a                   15.6470(7)
_cell_length_b                   17.5051(8)
_cell_length_c                   18.3972(9)
_cell_measurement_reflns_used    9857
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      31.60
_cell_measurement_theta_min      2.23
_cell_volume                     4452.1(4)
_computing_cell_refinement       'SAINT 7.46A (Bruker-AXS, 2011)'
_computing_data_collection       'APEX2 v2011.4.0 (Bruker-AXS, 2011)'
_computing_data_reduction        'SAINT 7.46A (Bruker-AXS, 2011)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2012 (Sheldrick, 2012)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 8.3
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker Smart APEX2 CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0381
_diffrn_reflns_av_unetI/netI     0.0187
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            376614
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.998
_diffrn_reflns_theta_min         1.173
_diffrn_source
'I\mS micro-focus sealed tube, multilayer optics'
_exptl_absorpt_coefficient_mu    0.102
_exptl_absorpt_correction_T_max  0.7463
_exptl_absorpt_correction_T_min  0.7000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2009)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.153
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1688
_exptl_crystal_size_max          0.450
_exptl_crystal_size_mid          0.400
_exptl_crystal_size_min          0.300
_exptl_transmission_factor_max   0.7463
_exptl_transmission_factor_min   0.7000
_refine_diff_density_max         1.387
_refine_diff_density_min         -0.443
_refine_diff_density_rms         0.100
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1047
_refine_ls_number_reflns         28367
_refine_ls_number_restraints     1149
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0777
_refine_ls_R_factor_gt           0.0667
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
; 
 w=1/[\s^2^(Fo^2^)+(0.1112P)^2^+2.9804P] 
 where P=(Fo^2^+2Fc^2^)/3 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1800
_refine_ls_wR_factor_ref         0.1927
_reflns_Friedel_coverage         0.000
_reflns_number_gt                23714
_reflns_number_total             28367
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja5009739_si_001.cif
_cod_data_source_block           x13121
_cod_database_code               4121450
_shelx_estimated_absorpt_t_min   0.956
_shelx_estimated_absorpt_t_max   0.970
_shelxl_version_number           2012-9
_shelx_res_checksum              57078
_shelx_hkl_checksum              84113