Pd-Catalyzed Amidations of Aryl Chlorides Using Monodentate Biaryl Phosphine Ligands: A Kinetic, Computational, and Synthetic Investigation
Takashi Ikawa; Timothy E. Barder; Mark R. Biscoe; Stephen L. Buchwald; Journal of the American Chemical Society 129 (2007) 13001–13007; doi:10.1021/ja0717414

data_4110092
_publ_section_title
;
 Pd-Catalyzed Amidations of Aryl Chlorides Using Monodentate Biaryl
 Phosphine Ligands: A Kinetic, Computational, and Synthetic Investigation
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              13001
_journal_page_last               13007
_journal_paper_doi               10.1021/ja0717414
_journal_volume                  129
_journal_year                    2007
_chemical_formula_sum            'C33 H53 P'
_chemical_formula_weight         480.72
_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                76.5310(10)
_cell_angle_beta                 83.3630(10)
_cell_angle_gamma                79.6560(10)
_cell_formula_units_Z            4
_cell_length_a                   11.2779(5)
_cell_length_b                   15.8314(7)
_cell_length_c                   17.6683(8)
_cell_measurement_reflns_used    5662
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      23.26
_cell_measurement_theta_min      2.27
_cell_volume                     3009.0(2)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_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      100(2)
_diffrn_measured_fraction_theta_full 0.950
_diffrn_measured_fraction_theta_max 0.950
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega 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  0.0216
_diffrn_reflns_av_sigmaI/netI    0.0386
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            10069
_diffrn_reflns_theta_full        20.81
_diffrn_reflns_theta_max         20.81
_diffrn_reflns_theta_min         1.19
_exptl_absorpt_coefficient_mu    0.109
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.061
_exptl_crystal_density_meas      0
_exptl_crystal_description       block
_exptl_crystal_F_000             1064
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.20
_refine_diff_density_max         1.081
_refine_diff_density_min         -0.338
_refine_diff_density_rms         0.057
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     645
_refine_ls_number_reflns         5990
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.0667
_refine_ls_R_factor_gt           0.0602
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0969P)^2^+4.5939P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1657
_refine_ls_wR_factor_ref         0.1740
_reflns_number_gt                5252
_reflns_number_total             5990
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja0717414si20070312_053806.cif
_cod_data_source_block           06143t
_cod_database_code               4110092