Pd-Catalyzed C‒N Coupling Reactions Facilitated by Organic Bases: Mechanistic Investigation Leads to Enhanced Reactivity in the Arylation of Weakly Binding Amines
Dennis, Joseph M.; White, Nicholas A.; Liu, Richard Y.; Buchwald, Stephen L.; ACS Catalysis 9 (2019) 3822–; doi:10.1021/acscatal.9b00981

data_4514696
_publ_section_title
;
 Pd-Catalyzed C--N Coupling Reactions Facilitated by Organic Bases:
 Mechanistic Investigation Leads to Enhanced Reactivity in the Arylation
 of Weakly Binding Amines
;
_journal_issue                   5
_journal_name_full               'ACS Catalysis'
_journal_page_first              3822
_journal_paper_doi               10.1021/acscatal.9b00981
_journal_volume                  9
_journal_year                    2019
_chemical_formula_sum            'C58 H84 F7 N2 O4 P Pd S'
_chemical_formula_weight         1175.70
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 106.9117(16)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   20.138(2)
_cell_length_b                   13.1828(13)
_cell_length_c                   24.998(2)
_cell_measurement_reflns_used    9242
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      24.89
_cell_measurement_theta_min      2.25
_cell_volume                     6349.4(10)
_computing_cell_refinement       'SAINT 8.38A (Bruker-AXS, 2017)'
_computing_data_collection       'APEX3 v2017.3.0 (Bruker-AXS, 2017)'
_computing_data_reduction        'SAINT 8.38A (Bruker-AXS, 2017)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXT-2015 (Sheldrick, 2015)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 8.3
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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  0.0732
_diffrn_reflns_av_unetI/netI     0.0324
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            257135
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.033
_diffrn_reflns_theta_min         1.057
_diffrn_source
'I\mS micro-focus sealed tube, multilayer optics'
_exptl_absorpt_coefficient_mu    0.413
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6965
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Herbst-Irmer et al., 2015)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.230
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             2472
_exptl_crystal_size_max          0.130
_exptl_crystal_size_mid          0.085
_exptl_crystal_size_min          0.070
_refine_diff_density_max         3.623
_refine_diff_density_min         -1.905
_refine_diff_density_rms         0.088
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     828
_refine_ls_number_reflns         18594
_refine_ls_number_restraints     756
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0793
_refine_ls_R_factor_gt           0.0562
_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^)+(0.0719P)^2^+10.9762P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1448
_refine_ls_wR_factor_ref         0.1609
_reflns_Friedel_coverage         0.000
_reflns_number_gt                13802
_reflns_number_total             18594
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs9b00981_si_002.cif
_cod_data_source_block           X17162_sq
_cod_original_cell_volume        6349.3(11)
_cod_database_code               4514696
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.948
_shelx_estimated_absorpt_t_max   0.972
_shelx_res_checksum              78500
_shelx_hkl_checksum              92862
_shelx_fab_checksum              17998