Redox-Neutral Imination of Alcohol with Azide: A Sustainable Alternative to the Staudinger/Aza-Wittig Reaction
Li, Huaifeng; Lupp, Daniel; Das, Pradip K.; Yang, Li; Gonçalves, Théo P.; Huang, Mei-Hui; El Hajoui, Marwa; Liang, Lan-Chang; Huang, Kuo-Wei; ACS Catalysis 11 (2021) 4071–4076; doi:10.1021/acscatal.1c00379

data_4518565
_publ_section_title
;
 Redox-Neutral Imination of Alcohol with Azide: A Sustainable Alternative
 to the Staudinger/Aza-Wittig Reaction
;
_journal_issue                   7
_journal_name_full               'ACS Catalysis'
_journal_page_first              4071
_journal_page_last               4076
_journal_paper_doi               10.1021/acscatal.1c00379
_journal_volume                  11
_journal_year                    2021
_chemical_formula_sum            'C25 H32 Cl0 N3 Ni O P'
_chemical_formula_weight         480.22
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           Triclinic'
_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                105.791(8)
_cell_angle_beta                 100.542(9)
_cell_angle_gamma                105.669(8)
_cell_formula_units_Z            4
_cell_length_a                   8.853(2)
_cell_length_b                   16.369(4)
_cell_length_c                   18.452(4)
_cell_measurement_reflns_used    9800
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      30.53
_cell_measurement_theta_min      2.31
_cell_volume                     2380.6(10)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      120(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_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  0.1019
_diffrn_reflns_av_sigmaI/netI    0.0586
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            128815
_diffrn_reflns_theta_full        30.58
_diffrn_reflns_theta_max         30.58
_diffrn_reflns_theta_min         2.10
_exptl_absorpt_coefficient_mu    0.904
_exptl_crystal_density_diffrn    1.340
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1016
_refine_diff_density_max         0.487
_refine_diff_density_min         -1.035
_refine_diff_density_rms         0.167
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.099
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     571
_refine_ls_number_reflns         14560
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.099
_refine_ls_R_factor_all          0.0929
_refine_ls_R_factor_gt           0.0471
_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^)+(0.0700P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1175
_refine_ls_wR_factor_ref         0.1405
_reflns_number_gt                9646
_reflns_number_total             14560
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cs1c00379_si_006.cif
_cod_data_source_block           om_xprep_a
_cod_depositor_comments
'Adding full bibliography for 4518564--4518568.cif.'
_cod_original_cell_volume        2380.7(10)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               4518565