Trifluoromethylation of Aryl and Heteroaryl Halides with Fluoroform-Derived CuCF3: Scope, Limitations, and Mechanistic Features
Anton Lishchynskyi; Maxim A. Novikov; Eddy Martin; Eduardo C. Escudero-Adán; Petr Novák; Vladimir V. Grushin; Journal of Organic Chemistry 78 (2013) 11126–11146; doi:10.1021/jo401423h

data_4028738
_publ_section_title
;
 Trifluoromethylation of Aryl and Heteroaryl Halides with
 Fluoroform-Derived CuCF3: Scope, Limitations, and Mechanistic Features
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              11126
_journal_page_last               11146
_journal_paper_doi               10.1021/jo401423h
_journal_volume                  78
_journal_year                    2013
_chemical_absolute_configuration ad
_chemical_formula_sum            'C6 H15 Br Cu N'
_chemical_formula_weight         244.64
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           217
_symmetry_cell_setting           cubic
_symmetry_space_group_name_Hall  'I -4 2 3'
_symmetry_space_group_name_H-M   'I -4 3 m'
_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            8
_cell_length_a                   12.1176(4)
_cell_length_b                   12.1176(4)
_cell_length_c                   12.1176(4)
_cell_measurement_reflns_used    1708
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      29.73
_cell_measurement_theta_min      3.36
_cell_volume                     1779.30(10)
_computing_cell_refinement       'Bruker APEX2 v2011.4-0'
_computing_data_collection       'Bruker APEX2 v2011.4-0'
_computing_data_reduction        'Bruker SAINT V7.60A'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_solution    Sir2011
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 512
_diffrn_detector_type            '4K CCD area detector APEX II'
_diffrn_measured_fraction_theta_full 0.963
_diffrn_measured_fraction_theta_max 0.963
_diffrn_measurement_device_type  'Kappa 4-axis goniometer bruker-nonius'
_diffrn_measurement_method
;
 Fullsphere data collection, phi and omega scans
;
_diffrn_measurement_specimen_support 'magnetic support with MicroMount'
_diffrn_radiation_monochromator  'Multilayer Montel 200 mirrors'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0256
_diffrn_reflns_av_sigmaI/netI    0.0134
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            5089
_diffrn_reflns_theta_full        30.07
_diffrn_reflns_theta_max         30.07
_diffrn_reflns_theta_min         3.36
_diffrn_source                   'Rotating anode x-ray tube'
_diffrn_source_current           70
_diffrn_source_power             50
_diffrn_source_size              '3 mm x 0.3 mm fine focus'
_diffrn_source_type              'Bruker-Nonius FR 591'
_exptl_absorpt_coefficient_mu    6.869
_exptl_absorpt_correction_T_max  0.5467
_exptl_absorpt_correction_T_min  0.5467
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details
; 
 SADABS Version 2008/1 Bruker-Nonius
 Blessing, Acta Cryst. (1995) A51 33-38
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.826
_exptl_crystal_description       Block
_exptl_crystal_F_000             976
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.351
_refine_diff_density_min         -0.360
_refine_diff_density_rms         0.057
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.008(15)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.122
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     25
_refine_ls_number_reflns         494
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.122
_refine_ls_R_factor_all          0.0138
_refine_ls_R_factor_gt           0.0135
_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^)+(0.0221P)^2^+0.5127P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0348
_refine_ls_wR_factor_ref         0.0349
_reflns_number_gt                489
_reflns_number_total             494
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo401423h_si_002.cif
_cod_data_source_block           al195_0m
_cod_database_code               4028738