A Highly Active Catalyst for Pd-Catalyzed Amination Reactions: Cross-Coupling Reactions Using Aryl Mesylates and the Highly Selective Monoarylation of Primary Amines Using Aryl Chlorides
Brett P. Fors; Donald A. Watson; Mark R. Biscoe; Stephen L. Buchwald; Journal of the American Chemical Society 130 (2008) 13552–13554; doi:10.1021/ja8055358

data_4108478
_publ_section_title
;
 A Highly Active Catalyst for Pd-Catalyzed Amination Reactions:
 Cross-Coupling Reactions Using Aryl Mesylates and the Highly Selective
 Monoarylation of Primary Amines Using Aryl Chlorides
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              13552
_journal_page_last               13554
_journal_paper_doi               10.1021/ja8055358
_journal_volume                  130
_journal_year                    2008
_chemical_formula_sum            'C41 H58 Br O2 P Pd'
_chemical_formula_weight         800.15
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_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-97
_cell_angle_alpha                100.1070(10)
_cell_angle_beta                 102.7390(10)
_cell_angle_gamma                107.5820(10)
_cell_formula_units_Z            2
_cell_length_a                   11.4784(7)
_cell_length_b                   11.8832(7)
_cell_length_c                   18.3144(11)
_cell_measurement_reflns_used    9903
_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      29.27
_cell_measurement_theta_min      2.36
_cell_volume                     2242.7(2)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      193(2)
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w 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  0.0516
_diffrn_reflns_av_sigmaI/netI    0.0448
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            62998
_diffrn_reflns_theta_full        30.62
_diffrn_reflns_theta_max         30.62
_diffrn_reflns_theta_min         1.93
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.368
_exptl_absorpt_correction_T_max  0.7664
_exptl_absorpt_correction_T_min  0.6034
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.185
_exptl_crystal_description       prism
_exptl_crystal_F_000             832
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_refine_diff_density_max         2.700
_refine_diff_density_min         -2.894
_refine_diff_density_rms         0.161
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.097
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     423
_refine_ls_number_reflns         13663
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.097
_refine_ls_R_factor_all          0.0735
_refine_ls_R_factor_gt           0.0543
_refine_ls_shift/su_max          0.025
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1114P)^2^+2.3812P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1795
_refine_ls_wR_factor_ref         0.1952
_reflns_number_gt                10606
_reflns_number_total             13663
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja8055358_si_001.cif
_cod_data_source_block           pm
_cod_database_code               4108478