Enantioenriched Synthesis of C1-Symmetric BINOLs: Iron-Catalyzed Cross-Coupling of 2-Naphthols and Some Mechanistic Insight
Hiromichi Egami; Kenji Matsumoto; Takuya Oguma; Takashi Kunisu; Tsutomu Katsuki; Journal of the American Chemical Society 132 (2010) 13633–13635; doi:10.1021/ja105442m

data_4103147
_publ_contact_author_address
;
Department of Chemistry, Faculty of Science, Graduate School,
Kyushu University, 6-10-1, Hakozaki, Higashi-ku, Fukuoka, 812-8581, Japan
;
_publ_contact_author_email       katsuscc@chem.kyushu-univ.jp
_publ_contact_author_fax         +81-92-642-2607
_publ_contact_author_name        'Tsutomu Katsuki'
_publ_contact_author_phone       +81-92-642-2586
_publ_section_title
;
 Enantioenriched Synthesis of C1-Symmetric BINOLs: Iron-Catalyzed
 Cross-Coupling of 2-Naphthols and Some Mechanistic Insight
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              13633
_journal_page_last               13635
_journal_paper_doi               10.1021/ja105442m
_journal_volume                  132
_journal_year                    2010
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C81 H66 Br Fe N2 O6'
_chemical_formula_sum            'C81 H66 Br Fe N2 O6'
_chemical_formula_weight         1299.12
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_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            4
_cell_length_a                   13.8731(11)
_cell_length_b                   20.8602(17)
_cell_length_c                   21.8492(18)
_cell_measurement_reflns_used    9940
_cell_measurement_temperature    100
_cell_measurement_theta_max      26.95
_cell_measurement_theta_min      2.16
_cell_volume                     6323.1(9)
_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      100
_diffrn_detector_area_resol_mean 8.333
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_collimation    'focusing mirrors'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'rotating-anode X-ray tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0357
_diffrn_reflns_av_sigmaI/netI    0.0533
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            36253
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         1.35
_exptl_absorpt_coefficient_mu    0.930
_exptl_absorpt_correction_T_max  0.9550
_exptl_absorpt_correction_T_min  0.9128
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details
;
SADABS Sheldrick 1996
;
_exptl_crystal_colour            'dark purple'
_exptl_crystal_density_diffrn    1.365
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             2700
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.725
_refine_diff_density_min         -0.558
_refine_diff_density_rms         0.065
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.008(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.998
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     830
_refine_ls_number_reflns         14310
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.998
_refine_ls_R_factor_all          0.0607
_refine_ls_R_factor_gt           0.0427
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0547P)^2^+1.9486P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0947
_refine_ls_wR_factor_ref         0.1022
_reflns_number_gt                11717
_reflns_number_total             14310
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja105442m_si_002.cif
_cod_data_source_block           Fesalan_3Br2NpO_H2O_KM93
_cod_database_code               4103147