Copper-Catalyzed Oxidative Cross-Coupling of N,N-Dimethylanilines with Heteroarenes under Molecular Oxygen
Lehao Huang; Tianmin Niu; Jun Wu; Yuhong Zhang; Journal of Organic Chemistry 76 (2011) 1759–1766; doi:10.1021/jo1023975

data_4026125
_publ_section_title
;
 Copper-Catalyzed Oxidative Cross-Coupling of N,N-Dimethylanilines with
 Heteroarenes under Molecular Oxygen
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              1759
_journal_page_last               1766
_journal_paper_doi               10.1021/jo1023975
_journal_volume                  76
_journal_year                    2011
_chemical_formula_moiety         'C25 H24 N2 O2'
_chemical_formula_sum            'C25 H24 N2 O2'
_chemical_formula_weight         384.46
_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                 101.765(11)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.0755(9)
_cell_length_b                   27.670(3)
_cell_length_c                   10.6387(11)
_cell_measurement_reflns_used    3406
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      29.3348
_cell_measurement_theta_min      3.2602
_cell_volume                     2039.1(4)
_computing_cell_refinement       'SAINT (Bruker, 2002)'
_computing_data_collection       'SMART (Bruker, 2002)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 29.40
_diffrn_measured_fraction_theta_max 0.873
_diffrn_measurement_device_type  'Bruker SMART area-detector diffractometer'
_diffrn_measurement_method       '\f and \w scan'
_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  0.0451
_diffrn_reflns_av_sigmaI/netI    0.0619
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       37
_diffrn_reflns_limit_k_min       -35
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            12412
_diffrn_reflns_theta_full        29.40
_diffrn_reflns_theta_max         29.40
_diffrn_reflns_theta_min         3.27
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.88332
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2002)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.252
_exptl_crystal_description       block
_exptl_crystal_F_000             888
_exptl_crystal_size_max          0.64
_exptl_crystal_size_mid          0.42
_exptl_crystal_size_min          0.32
_refine_diff_density_max         0.250
_refine_diff_density_min         -0.180
_refine_diff_density_rms         0.040
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.659
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     270
_refine_ls_number_reflns         4907
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.659
_refine_ls_R_factor_all          0.1184
_refine_ls_R_factor_gt           0.0549
_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^)+(0.2000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1640
_refine_ls_wR_factor_ref         0.2156
_reflns_number_gt                2378
_reflns_number_total             4907
_reflns_threshold_expression     >2\s(I)
_cod_data_source_file            jo1023975_si_001.cif
_cod_data_source_block           100326_hlh_180_1
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4026125