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_4118829
_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            'C9 H7 N O3'
_chemical_formula_weight         177.16
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 93.619(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.6481(9)
_cell_length_b                   8.8247(11)
_cell_length_c                   11.7268(14)
_cell_measurement_reflns_used    1095
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      24.02
_cell_measurement_theta_min      2.89
_cell_volume                     789.89(17)
_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, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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  0.0208
_diffrn_reflns_av_sigmaI/netI    0.0252
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            3872
_diffrn_reflns_theta_full        25.09
_diffrn_reflns_theta_max         25.09
_diffrn_reflns_theta_min         2.89
_exptl_absorpt_coefficient_mu    0.114
_exptl_absorpt_correction_T_max  0.9829
_exptl_absorpt_correction_T_min  0.9593
_exptl_absorpt_correction_type   none
_exptl_crystal_density_diffrn    1.490
_exptl_crystal_F_000             368
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.189
_refine_diff_density_min         -0.121
_refine_diff_density_rms         0.039
_refine_ls_extinction_coef       0.005(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     120
_refine_ls_number_reflns         1400
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.076
_refine_ls_R_factor_all          0.0671
_refine_ls_R_factor_gt           0.0449
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0802P)^2^+0.0343P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1239
_refine_ls_wR_factor_ref         0.1445
_reflns_number_gt                946
_reflns_number_total             1400
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja308976x_si_002.cif
_cod_data_source_block           xb5563_0m
_cod_database_code               4118829