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_4129661
_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_moiety         'C63 H86 F O2 P Pd, 0.5(C6 H6)'
_chemical_formula_sum            'C66 H89 F O2 P Pd'
_chemical_formula_weight         1070.74
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/6
_cell_angle_alpha                90
_cell_angle_beta                 101.0135(15)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.2179(11)
_cell_length_b                   24.1395(18)
_cell_length_c                   16.4947(13)
_cell_measurement_reflns_used    9034
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.27
_cell_measurement_theta_min      2.42
_cell_volume                     5556.9(7)
_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-2014/6 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 8.3
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.994
_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  0.0636
_diffrn_reflns_av_unetI/netI     0.0332
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       33
_diffrn_reflns_limit_k_min       -33
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            184740
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.575
_diffrn_reflns_theta_min         1.514
_diffrn_source
'I\mS micro-focus sealed tube, multilayer optics'
_exptl_absorpt_coefficient_mu    0.410
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6816
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2009)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.280
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             2284
_exptl_crystal_size_max          0.190
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.020
_refine_diff_density_max         0.492
_refine_diff_density_min         -0.904
_refine_diff_density_rms         0.070
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     679
_refine_ls_number_reflns         15485
_refine_ls_number_restraints     162
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0575
_refine_ls_R_factor_gt           0.0375
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0253P)^2^+6.7176P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0781
_refine_ls_wR_factor_ref         0.0864
_reflns_Friedel_coverage         0.000
_reflns_number_gt                12010
_reflns_number_total             15485
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja5b09308_si_002.cif
_cod_data_source_block           X14160
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4129661
_shelx_estimated_absorpt_t_min   0.926
_shelx_estimated_absorpt_t_max   0.992
_shelxl_version_number           2014/6
_shelx_res_checksum              63478
_shelx_hkl_checksum              46421