Mechanistic Study of Asymmetric Oxidative Biaryl Coupling: Evidence for Self-Processing of the Copper Catalyst to Achieve Control of Oxidase vs Oxygenase Activity
J. Brian Hewgley; Shannon S. Stahl; Marisa C. Kozlowski; Journal of the American Chemical Society 130 (2008) 12232–12233; doi:10.1021/ja804570b

data_4108354
_publ_section_title
;
 Mechanistic Study of Asymmetric Oxidative Biaryl Coupling: Evidence for
 Self-Processing of the Copper Catalyst to Achieve Control of Oxidase vs
 Oxygenase Activity
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              12232
_journal_page_last               12233
_journal_paper_doi               10.1021/ja804570b
_journal_volume                  130
_journal_year                    2008
_chemical_formula_sum            'C25 H18 Cl2 O10'
_chemical_formula_weight         549.29
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_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
_audit_creation_method           SHELXL-97
_cell_angle_alpha                84.172(3)
_cell_angle_beta                 83.812(3)
_cell_angle_gamma                79.439(3)
_cell_formula_units_Z            2
_cell_length_a                   7.1311(4)
_cell_length_b                   12.5109(7)
_cell_length_c                   13.6583(8)
_cell_measurement_temperature    143(1)
_cell_volume                     1186.75(12)
_computing_data_collection       'CrystalClear (Rigaku, 1999)'
_computing_data_reduction        'CrystalClear (Rigaku, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR97 (Altomare, 1999)'
_diffrn_ambient_temperature      143(1)
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device       'CCD Area Detector'
_diffrn_measurement_device_type  'Rigaku Mercury'
_diffrn_measurement_method       'phi and omega rotations'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0170
_diffrn_reflns_av_sigmaI/netI    0.0216
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            11133
_diffrn_reflns_theta_full        25.34
_diffrn_reflns_theta_max         25.34
_diffrn_reflns_theta_min         2.92
_exptl_absorpt_coefficient_mu    0.334
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8346
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;  Shape and scale corrections using equivalent reflections.
    Shape function based on spherical harmonics.
    Highest even and odd order for spherical harmonics:  4  and  3
    Laue group:  mmm
    Friedel opposites are equivalent.
;
_exptl_crystal_density_diffrn    1.537
_exptl_crystal_F_000             564
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.782
_refine_diff_density_min         -0.625
_refine_diff_density_rms         0.071
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     339
_refine_ls_number_reflns         4310
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.061
_refine_ls_R_factor_all          0.0618
_refine_ls_R_factor_gt           0.0564
_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^)+(0.0922P)^2^+1.1736P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1585
_refine_ls_wR_factor_ref         0.1645
_reflns_number_gt                3777
_reflns_number_total             4310
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja804570b_si_003.cif
_cod_data_source_block           shelxl
_cod_original_sg_symbol_H-M      'P -1 '
_cod_database_code               4108354