Room-Temperature Chemoselective Reductive Alkylation of Amines Catalyzed by a Well-Defined Iron(II) Complex Using Hydrogen.
Lator, Alexis; Gaillard, Quentin Gaignard; Mérel, Delphine S; Lohier, Jean-François; Gaillard, Sylvain; Poater, Albert; Renaud, Jean-Luc; The Journal of organic chemistry 84 (2019) 6813–6829; doi:10.1021/acs.joc.9b00581

data_4034597
_publ_section_title
;
 Room-Temperature Chemoselective Reductive Alkylation of Amines Catalyzed
 by a Well-Defined Iron(II) Complex Using Hydrogen.
;
_journal_issue                   11
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              6813
_journal_page_last               6829
_journal_paper_doi               10.1021/acs.joc.9b00581
_journal_volume                  84
_journal_year                    2019
_chemical_formula_moiety         'C27 H27 B F4 Fe N3 O3'
_chemical_formula_sum            'C27 H27 B F4 Fe N3 O3'
_chemical_formula_weight         584.17
_chemical_name_common
'Iron tricarbonyl triaminocyclopentadienyl tetrafuloroborate'
_chemical_name_systematic
'Iron tricarbonyl triaminocyclopentadienyl tetrafuloroborate'
_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   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                104.967(2)
_cell_angle_beta                 99.429(2)
_cell_angle_gamma                98.308(2)
_cell_formula_units_Z            4
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_cell_length_b                   16.3251(7)
_cell_length_c                   21.7086(10)
_cell_measurement_reflns_used    9936
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      28.27
_cell_measurement_theta_min      2.39
_cell_volume                     2914.9(2)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
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_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.958
_diffrn_measured_fraction_theta_max 0.954
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
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_diffrn_reflns_av_R_equivalents  0.0381
_diffrn_reflns_av_unetI/netI     0.0513
_diffrn_reflns_Laue_measured_fraction_full 0.958
_diffrn_reflns_Laue_measured_fraction_max 0.954
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            31715
_diffrn_reflns_point_group_measured_fraction_full 0.958
_diffrn_reflns_point_group_measured_fraction_max 0.954
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.373
_diffrn_reflns_theta_min         2.392
_exptl_absorpt_coefficient_mu    0.574
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Sadabs 2015/1'
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.331
_exptl_crystal_description       block
_exptl_crystal_F_000             1204
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   0.7486
_exptl_transmission_factor_min   0.6532
_platon_squeeze_details
;
;
_refine_diff_density_max         1.649
_refine_diff_density_min         -0.801
_refine_diff_density_rms         0.108
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.097
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     711
_refine_ls_number_reflns         11360
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.097
_refine_ls_R_factor_all          0.0989
_refine_ls_R_factor_gt           0.0831
_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^)+(0.0656P)^2^+14.6792P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1917
_refine_ls_wR_factor_ref         0.1989
_reflns_Friedel_coverage         0.000
_reflns_number_gt                9225
_reflns_number_total             11360
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b00581_si_002.cif
_cod_data_source_block           merel13_0m_a
_cod_database_code               4034597
_shelx_shelxl_version_number     2014/7
_shelx_res_checksum              30587
_shelx_hkl_checksum              55406