Aerobic, Transition-Metal-Free, Direct, and Regiospecific Mono-α-arylation of Ketones: Synthesis and Mechanism by DFT Calculations
Qing-Long Xu; Hongyin Gao; Muhammed Yousufuddin; Daniel H. Ess; László Kürti; Journal of the American Chemical Society 135 (2013) 14048–14051; doi:10.1021/ja4074563

data_4120854
_publ_section_title
;
 Aerobic, Transition-Metal-Free, Direct, and Regiospecific
 Mono-\a-arylation of Ketones: Synthesis and Mechanism by DFT Calculations
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              14048
_journal_page_last               14051
_journal_paper_doi               10.1021/ja4074563
_journal_volume                  135
_journal_year                    2013
_chemical_formula_sum            'C20 H15 N O3'
_chemical_formula_weight         317.33
_space_group_IT_number           1
_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                97.229(3)
_cell_angle_beta                 101.480(3)
_cell_angle_gamma                107.079(3)
_cell_formula_units_Z            2
_cell_length_a                   7.1761(15)
_cell_length_b                   10.402(2)
_cell_length_c                   10.811(2)
_cell_measurement_reflns_used    5593
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.64
_cell_measurement_theta_min      2.57
_cell_volume                     741.2(3)
_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(2)
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w 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  0.0217
_diffrn_reflns_av_sigmaI/netI    0.0483
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            7829
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         28.64
_diffrn_reflns_theta_min         1.96
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_T_max  0.9891
_exptl_absorpt_correction_T_min  0.9658
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.422
_exptl_crystal_description       prism
_exptl_crystal_F_000             332
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.11
_refine_diff_density_max         1.188
_refine_diff_density_min         -0.469
_refine_diff_density_rms         0.192
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   1.5(13)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     433
_refine_ls_number_reflns         6673
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.066
_refine_ls_R_factor_all          0.0785
_refine_ls_R_factor_gt           0.0732
_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^)+(0.1907P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2233
_refine_ls_wR_factor_ref         0.2307
_reflns_number_gt                6128
_reflns_number_total             6673
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja4074563_si_002.cif
_cod_data_source_block           laszlo11_0m_a
_cod_database_code               4120854