Direct Oxidative Coupling of Enamines and Electron-Deficient Amines: TBAI/TBHP-Mediated Synthesis of Substituted Diaminoalkenes under Metal-Free Conditions.
Yuan, Yucheng; Hou, Wenjuan; Zhang-Negrerie, Daisy; Zhao, Kang; Du, Yunfei; Organic letters 16 (2014) 5410–5413; doi:10.1021/ol5026525

data_1517943
_publ_section_title
;
 Direct Oxidative Coupling of Enamines and Electron-Deficient Amines:
 TBAI/TBHP-Mediated Synthesis of Substituted Diaminoalkenes under
 Metal-Free Conditions.
;
_journal_issue                   20
_journal_name_full               'Organic letters'
_journal_page_first              5410
_journal_page_last               5413
_journal_paper_doi               10.1021/ol5026525
_journal_volume                  16
_journal_year                    2014
_chemical_formula_moiety         'C18 H13 Br1 N2 O4'
_chemical_formula_sum            'C18 H13 Br N2 O4'
_chemical_formula_weight         401.21
_chemical_melting_point          225
_chemical_name_common            diaminoalkene
_chemical_name_systematic
; 
 (E)-methyl 3-amino-3-(4-bromophenyl)-2-(1,3-dioxoisoindolin-2-yl)acrylate 
;
_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                70.16(3)
_cell_angle_beta                 75.47(3)
_cell_angle_gamma                83.16(3)
_cell_formula_units_Z            4
_cell_length_a                   8.4774(17)
_cell_length_b                   14.219(3)
_cell_length_c                   15.561(3)
_cell_measurement_temperature    293(2)
_cell_volume                     1706.8(7)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_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  0.0772
_diffrn_reflns_av_sigmaI/netI    0.1089
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            14162
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         25.50
_diffrn_reflns_theta_min         3.05
_exptl_absorpt_coefficient_mu    2.434
_exptl_absorpt_correction_T_max  0.7929
_exptl_absorpt_correction_T_min  0.6417
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.561
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             808
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.942
_refine_diff_density_min         -0.829
_refine_diff_density_rms         0.075
_refine_ls_extinction_coef       0.0166(12)
_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   1.009
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     452
_refine_ls_number_reflns         6317
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.009
_refine_ls_R_factor_all          0.1406
_refine_ls_R_factor_gt           0.0653
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0600P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1241
_refine_ls_wR_factor_ref         0.1419
_reflns_number_gt                3385
_reflns_number_total             6317
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol5026525_si_002.cif
_cod_data_source_block           3d
_cod_depositor_comments          'Adding full bibliography for 1517943.cif.'
_cod_original_cell_volume        1706.7(6)
_cod_original_sg_symbol_H-M      P-1
_cod_original_formula_sum        'C18 H13 Br1 N2 O4'
_cod_database_code               1517943