Palladium-Catalyzed Oxidative Coupling of Aromatic Primary Amines and Alkenes under Molecular Oxygen: Stereoselective Assembly of (Z)-Enamines
Xiaochen Ji; Huawen Huang; Wanqing Wu; Xianwei Li; Huanfeng Jiang; Journal of Organic Chemistry 78 (2013) 11155–11162; doi:10.1021/jo402117r

data_4028764
_publ_section_title
;
 Palladium-Catalyzed Oxidative Coupling of Aromatic Primary Amines and
 Alkenes under Molecular Oxygen: Stereoselective Assembly of (Z)-Enamines
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              11155
_journal_page_last               11162
_journal_paper_doi               10.1021/jo402117r
_journal_volume                  78
_journal_year                    2013
_chemical_formula_sum            'C19 H16 F N O2'
_chemical_formula_weight         309.33
_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                 98.87(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.152(2)
_cell_length_b                   7.7729(16)
_cell_length_c                   16.896(3)
_cell_measurement_temperature    293(2)
_cell_volume                     1576.8(5)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_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  0.0373
_diffrn_reflns_av_sigmaI/netI    0.0331
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            14917
_diffrn_reflns_theta_full        27.46
_diffrn_reflns_theta_max         27.46
_diffrn_reflns_theta_min         3.12
_exptl_absorpt_coefficient_mu    0.092
_exptl_crystal_density_diffrn    1.303
_exptl_crystal_F_000             648
_refine_diff_density_max         0.211
_refine_diff_density_min         -0.207
_refine_diff_density_rms         0.055
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.086
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         3579
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.086
_refine_ls_R_factor_all          0.1049
_refine_ls_R_factor_gt           0.0539
_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^)+(0.1043P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1479
_refine_ls_wR_factor_ref         0.1959
_reflns_number_gt                1804
_reflns_number_total             3579
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo402117r_si_002.cif
_cod_data_source_block           jxc
_cod_original_cell_volume        1576.9(6)
_cod_database_code               4028764