Lewis Acid/Hexafluoroisopropanol: A Promoter System for Selective ortho-C-Alkylation of Anilines with Deactivated Styrene Derivatives and Unactivated Alkenes
Wang, Shengdong; Force, Guillaume; Guillot, Régis; Carpentier, Jean-François; Sarazin, Yann; Bour, Christophe; Gandon, Vincent; Lebœuf, David; ACS Catalysis  (2020) 10794–; doi:10.1021/acscatal.0c02959

data_4518024
_publ_section_title
;
 Lewis Acid/Hexafluoroisopropanol: A Promoter System for Selective
 ortho-C-Alkylation of Anilines with Deactivated Styrene Derivatives and
 Unactivated Alkenes
;
_journal_name_full               'ACS Catalysis'
_journal_page_first              10794
_journal_paper_doi               10.1021/acscatal.0c02959
_journal_year                    2020
_chemical_formula_moiety         'C21 H18 N2'
_chemical_formula_sum            'C21 H18 N2'
_chemical_formula_weight         298.37
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                84.0160(10)
_cell_angle_beta                 85.2380(10)
_cell_angle_gamma                62.6830(10)
_cell_formula_units_Z            2
_cell_length_a                   8.9756(4)
_cell_length_b                   9.0718(4)
_cell_length_c                   11.0372(5)
_cell_measurement_reflns_used    9973
_cell_measurement_temperature    100(1)
_cell_measurement_theta_max      66.71
_cell_measurement_theta_min      4.03
_cell_volume                     793.50(6)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX3'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      100(1)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker VENTURE PHOTON100 CMOS'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0269
_diffrn_reflns_av_unetI/netI     0.0179
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            18032
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        66.707
_diffrn_reflns_theta_max         66.707
_diffrn_reflns_theta_min         4.030
_exptl_absorpt_coefficient_mu    0.566
_exptl_absorpt_correction_T_max  0.9528
_exptl_absorpt_correction_T_min  0.8973
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker APEX3'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.249
_exptl_crystal_description       plate
_exptl_crystal_F_000             316
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.040
_refine_diff_density_max         0.267
_refine_diff_density_min         -0.209
_refine_diff_density_rms         0.047
_refine_ls_extinction_coef       0.0144(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     214
_refine_ls_number_reflns         2810
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.067
_refine_ls_R_factor_all          0.0346
_refine_ls_R_factor_gt           0.0329
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0401P)^2^+0.2472P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0827
_refine_ls_wR_factor_ref         0.0840
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2672
_reflns_number_total             2810
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs0c02959_si_002.cif
_cod_data_source_block           3aa
_cod_database_code               4518024
_shelx_estimated_absorpt_t_min   0.890
_shelx_estimated_absorpt_t_max   0.979
_shelx_res_checksum              14700
_shelx_hkl_checksum              10333