Palladium-Catalyzed Regioselective Carbonylation of C-H Bonds of N-Alkyl Anilines for Synthesis of Isatoic Anhydrides
Zheng-Hui Guan; Ming Chen; Zhi-Hui Ren; Journal of the American Chemical Society 134 (2012) 17490–17493; doi:10.1021/ja308976x

data_4118830
_publ_section_title
;
 Palladium-Catalyzed Regioselective Carbonylation of C-H Bonds of N-Alkyl
 Anilines for Synthesis of Isatoic Anhydrides
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              17490
_journal_page_last               17493
_journal_paper_doi               10.1021/ja308976x
_journal_volume                  134
_journal_year                    2012
_chemical_formula_sum            'C50.5 H46 Cl3 N2 P2 Pd2'
_chemical_formula_weight         1061.98
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 98.644(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.9834(14)
_cell_length_b                   18.151(3)
_cell_length_c                   27.004(4)
_cell_measurement_reflns_used    5449
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      25.58
_cell_measurement_theta_min      2.35
_cell_volume                     4837.8(13)
_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, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_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  0.0410
_diffrn_reflns_av_sigmaI/netI    0.0504
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            23737
_diffrn_reflns_theta_full        25.05
_diffrn_reflns_theta_max         25.05
_diffrn_reflns_theta_min         1.89
_exptl_absorpt_coefficient_mu    1.011
_exptl_absorpt_correction_type   none
_exptl_crystal_density_diffrn    1.458
_exptl_crystal_F_000             2144
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.906
_refine_diff_density_min         -0.386
_refine_diff_density_rms         0.104
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     561
_refine_ls_number_reflns         8465
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.065
_refine_ls_R_factor_all          0.0646
_refine_ls_R_factor_gt           0.0454
_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^)+(0.0635P)^2^+6.0385P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1176
_refine_ls_wR_factor_ref         0.1292
_reflns_number_gt                6485
_reflns_number_total             8465
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja308976x_si_003.cif
_cod_data_source_block           1
_cod_original_cell_volume        4837.9(12)
_cod_original_formula_sum        'C50.50 H46 Cl3 N2 P2 Pd2'
_cod_database_code               4118830