Cu-Facilitated C-O Bond Formation Using N-Hydroxyphthalimide: Efficient and Selective Functionalization of Benzyl and Allylic C-H Bonds
Ji Min Lee; Eun Ju Park; Seung Hwan Cho; Sukbok Chang; Journal of the American Chemical Society 130 (2008) 7824–7825; doi:10.1021/ja8031218

data_4107931
_publ_section_title
;
 Cu-Facilitated C-O Bond Formation Using N-Hydroxyphthalimide: Efficient
 and Selective Functionalization of Benzyl and Allylic C-H Bonds
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              7824
_journal_page_last               7825
_journal_paper_doi               10.1021/ja8031218
_journal_volume                  130
_journal_year                    2008
_chemical_formula_sum            'C23 H17 N O3'
_chemical_formula_weight         355.38
_space_group_IT_number           33
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2c -2n'
_symmetry_space_group_name_H-M   'P n a 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                   12.3497(10)
_cell_length_b                   25.3030(19)
_cell_length_c                   5.5954(5)
_cell_measurement_reflns_used    3242
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      20.91
_cell_measurement_theta_min      2.92
_cell_volume                     1748.5(2)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_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  0.0281
_diffrn_reflns_av_sigmaI/netI    0.0261
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       5
_diffrn_reflns_limit_l_min       -5
_diffrn_reflns_number            7924
_diffrn_reflns_theta_full        21.00
_diffrn_reflns_theta_max         21.00
_diffrn_reflns_theta_min         1.61
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_type   none
_exptl_crystal_density_diffrn    1.350
_exptl_crystal_density_meas      0
_exptl_crystal_F_000             744
_refine_diff_density_max         0.179
_refine_diff_density_min         -0.279
_refine_diff_density_rms         0.085
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   2.8(18)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     244
_refine_ls_number_reflns         1886
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0354
_refine_ls_R_factor_gt           0.0283
_refine_ls_shift/su_max          0.007
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0804P)^2^+0.0014P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0767
_refine_ls_wR_factor_ref         0.1017
_reflns_number_gt                1774
_reflns_number_total             1886
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja8031218-file003.cif
_cod_data_source_block           sbc29
_cod_database_code               4107931