A Fluorinated Ligand Enables Room-Temperature and Regioselective Pd-Catalyzed Fluorination of Aryl Triflates and Bromides.
Sather, Aaron C.; Lee, Hong Geun; De La Rosa, Valentina Y.; Yang, Yang; Müller, Peter; Buchwald, Stephen L.; Journal of the American Chemical Society 137 (2015) 13433–13438; doi:10.1021/jacs.5b09308

data_4129658
_publ_section_title
;
 A Fluorinated Ligand Enables Room-Temperature and Regioselective
 Pd-Catalyzed Fluorination of Aryl Triflates and Bromides.
;
_journal_issue                   41
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              13433
_journal_page_last               13438
_journal_paper_doi               10.1021/jacs.5b09308
_journal_volume                  137
_journal_year                    2015
_chemical_formula_sum            'C148 H182 F8 O2 P2 Pd2'
_chemical_formula_weight         2419.67
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/6
_cell_angle_alpha                106.007(5)
_cell_angle_beta                 108.619(5)
_cell_angle_gamma                101.864(5)
_cell_formula_units_Z            1
_cell_length_a                   13.560(4)
_cell_length_b                   14.303(4)
_cell_length_c                   18.204(5)
_cell_measurement_reflns_used    4152
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      19.71
_cell_measurement_theta_min      2.22
_cell_volume                     3044.5(15)
_computing_cell_refinement       'SAINT 7.46A (Bruker-AXS, 2015)'
_computing_data_collection       'APEX2 v2011.4.0 (Bruker-AXS, 2015)'
_computing_data_reduction        'SAINT 7.46A (Bruker-AXS, 2015)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
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_computing_structure_solution    'SHELXS-2015 (Sheldrick, 2015)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 8.3
_diffrn_measured_fraction_theta_full 0.781
_diffrn_measured_fraction_theta_max 0.984
_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  0.1201
_diffrn_reflns_av_unetI/netI     0.0900
_diffrn_reflns_Laue_measured_fraction_full 0.781
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            56748
_diffrn_reflns_point_group_measured_fraction_full 0.781
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         23.256
_diffrn_reflns_theta_min         1.565
_diffrn_source
'I\mS micro-focus sealed tube, multilayer optics'
_exptl_absorpt_coefficient_mu    0.389
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6778
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2009)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.320
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1280
_exptl_crystal_size_max          0.045
_exptl_crystal_size_mid          0.005
_exptl_crystal_size_min          0.004
_refine_diff_density_max         0.331
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_refine_diff_density_rms         0.077
_refine_ls_extinction_method     none
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_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     799
_refine_ls_number_reflns         8598
_refine_ls_number_restraints     1952
_refine_ls_restrained_S_all      0.932
_refine_ls_R_factor_all          0.0934
_refine_ls_R_factor_gt           0.0514
_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^)+(0.0491P)^2^+2.7518P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1061
_refine_ls_wR_factor_ref         0.1238
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5921
_reflns_number_total             8598
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja5b09308_si_002.cif
_cod_data_source_block           X15097
_cod_database_code               4129658
_shelx_estimated_absorpt_t_min   0.983
_shelx_estimated_absorpt_t_max   0.998
_shelxl_version_number           2014/6
_shelx_res_checksum              96937
_shelx_hkl_checksum              70634