Expanding the forefront of strong organic Brønsted acids: proton-catalyzed hydroamination of unactivated alkenes and activation of Au(I) for alkyne hydroamination.
Mirabdolbaghi, Roya; Dudding, Travis; Organic letters 17 (2015) 1930–1933; doi:10.1021/acs.orglett.5b00617

data_1554912
_publ_section_title
;
 Expanding the forefront of strong organic Br\/onsted acids:
 proton-catalyzed hydroamination of unactivated alkenes and activation of
 Au(I) for alkyne hydroamination.
;
_journal_issue                   8
_journal_name_full               'Organic letters'
_journal_page_first              1930
_journal_page_last               1933
_journal_paper_doi               10.1021/acs.orglett.5b00617
_journal_volume                  17
_journal_year                    2015
_chemical_formula_moiety         'C20 H39 N5, 2(B F4), H2 O'
_chemical_formula_sum            'C20 H41 B2 F8 N5 O'
_chemical_formula_weight         541.20
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.9728(13)
_cell_length_b                   10.8425(14)
_cell_length_c                   25.575(3)
_cell_measurement_reflns_used    5935
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      24.61
_cell_measurement_theta_min      2.46
_cell_volume                     2765.4(6)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_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      173(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0194
_diffrn_reflns_av_unetI/netI     0.0291
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            16876
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.280
_diffrn_reflns_theta_min         1.592
_exptl_absorpt_coefficient_mu    0.117
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.9252
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.300
_exptl_crystal_description       plate
_exptl_crystal_F_000             1144
_exptl_crystal_size_max          0.466
_exptl_crystal_size_mid          0.402
_exptl_crystal_size_min          0.110
_refine_diff_density_max         0.364
_refine_diff_density_min         -0.378
_refine_diff_density_rms         0.048
_refine_ls_abs_structure_details
; 
 Flack x determined using 2239 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.14(18)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     331
_refine_ls_number_reflns         6855
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.071
_refine_ls_R_factor_all          0.0584
_refine_ls_R_factor_gt           0.0481
_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^)+(0.0883P)^2^+0.2109P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1346
_refine_ls_wR_factor_ref         0.1405
_reflns_Friedel_coverage         0.775
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.996
_reflns_number_gt                5713
_reflns_number_total             6855
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol5b00617_si_001.cif
_cod_data_source_block           rm07614_0m_a
_cod_database_code               1554912
_shelx_estimated_absorpt_t_min   0.947
_shelx_estimated_absorpt_t_max   0.987
_shelxl_version_number           2014-3
_shelx_res_checksum              3712
_shelx_hkl_checksum              96494