Borane-Catalyzed Chemoselectivity-Controllable N-Alkylation and ortho C-Alkylation of Unprotected Arylamines Using Benzylic Alcohols
Meng, Shan-Shui; Tang, Xiaowen; Luo, Xiang; Wu, Ruibo; Zhao, Jun-Ling; Chan, Albert S. C.; ACS Catalysis 9 (2019) 8397–; doi:10.1021/acscatal.9b03038

data_4514815
_publ_section_title
;
 Borane-Catalyzed Chemoselectivity-Controllable N-Alkylation and ortho
 C-Alkylation of Unprotected Arylamines Using Benzylic Alcohols
;
_journal_issue                   9
_journal_name_full               'ACS Catalysis'
_journal_page_first              8397
_journal_paper_doi               10.1021/acscatal.9b03038
_journal_volume                  9
_journal_year                    2019
_chemical_formula_sum            'C25 H9 B F15 N O'
_chemical_formula_weight         635.14
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2016/6
_audit_update_record
;
2019-04-28 deposited with the CCDC.    2019-08-13 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 91.1950(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.7548(2)
_cell_length_b                   8.52180(10)
_cell_length_c                   17.5186(2)
_cell_measurement_temperature    293(2)
_cell_volume                     2351.52(5)
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.954
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0221
_diffrn_reflns_av_unetI/netI     0.0194
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.954
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       3
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            15687
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.954
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.744
_diffrn_reflns_theta_min         2.805
_exptl_absorpt_coefficient_mu    1.742
_exptl_crystal_density_diffrn    1.794
_exptl_crystal_F_000             1256
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.310
_refine_diff_density_min         -0.259
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     389
_refine_ls_number_reflns         4728
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.0354
_refine_ls_R_factor_gt           0.0324
_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^)+(0.0395P)^2^+1.4726P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0833
_refine_ls_wR_factor_ref         0.0859
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4364
_reflns_number_total             4728
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs9b03038_si_002.cif
_cod_data_source_block           mengshsh_181217_2
_cod_database_code               4514815
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_min   0.623
_shelx_estimated_absorpt_t_max   0.845
_shelx_res_checksum              8535
_shelx_hkl_checksum              30354