Palladium-Catalyzed Intermolecular Aerobic Oxidative Cyclization of 2-Ethynylanilines with Isocyanides: Regioselective Synthesis of 4-Halo-2-aminoquinolines
Bifu Liu; Hanling Gao; Yue Yu; Wanqing Wu; Huanfeng Jiang; Journal of Organic Chemistry 78 (2013) 10319–10328; doi:10.1021/jo401707j

data_4028675
_publ_section_title
;
 Palladium-Catalyzed Intermolecular Aerobic Oxidative Cyclization of
 2-Ethynylanilines with Isocyanides: Regioselective Synthesis of
 4-Halo-2-aminoquinolines
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              10319
_journal_page_last               10328
_journal_paper_doi               10.1021/jo401707j
_journal_volume                  78
_journal_year                    2013
_chemical_formula_sum            'C19 H18 Br Cl N2'
_chemical_formula_weight         389.71
_space_group_IT_number           114
_symmetry_cell_setting           tetragonal
_symmetry_space_group_name_Hall  'P -4 2n'
_symmetry_space_group_name_H-M   'P -4 21 c'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   20.320(3)
_cell_length_b                   20.320(3)
_cell_length_c                   8.7899(18)
_cell_measurement_temperature    293(2)
_cell_volume                     3629.4(11)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_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  0.0781
_diffrn_reflns_av_sigmaI/netI    0.0446
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            53330
_diffrn_reflns_theta_full        27.47
_diffrn_reflns_theta_max         27.47
_diffrn_reflns_theta_min         3.06
_exptl_absorpt_coefficient_mu    2.413
_exptl_crystal_density_diffrn    1.426
_exptl_crystal_F_000             1584
_refine_diff_density_max         0.744
_refine_diff_density_min         -0.624
_refine_diff_density_rms         0.063
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.013(13)
_refine_ls_extinction_coef       0.0206(17)
_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   1.017
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         4149
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.017
_refine_ls_R_factor_all          0.0726
_refine_ls_R_factor_gt           0.0506
_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^)+(0.0981P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1456
_refine_ls_wR_factor_ref         0.1590
_reflns_number_gt                2757
_reflns_number_total             4149
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo401707j_si_002.cif
_cod_data_source_block           1
_cod_original_cell_volume        3629.3(10)
_cod_database_code               4028675