Mechanistic Investigation of the Nickel-Catalyzed Suzuki Reaction of N,O-Acetals: Evidence for Boronic Acid Assisted Oxidative Addition and an Iminium Activation Pathway
Kevin T. Sylvester; Kevin Wu; Abigail G. Doyle; Journal of the American Chemical Society 134 (2012) 16967–16970; doi:10.1021/ja3079362

data_4118772
_publ_section_title
;
 Mechanistic Investigation of the Nickel-Catalyzed Suzuki Reaction of
 N,O-Acetals: Evidence for Boronic Acid Assisted Oxidative Addition and an
 Iminium Activation Pathway
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              16967
_journal_page_last               16970
_journal_paper_doi               10.1021/ja3079362
_journal_volume                  134
_journal_year                    2012
_chemical_formula_sum            'C51 H44 Cl4 F3 N Ni O6 P2 S'
_chemical_formula_weight         1118.38
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_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                110.9740(10)
_cell_angle_beta                 94.2700(10)
_cell_angle_gamma                95.6880(10)
_cell_formula_units_Z            2
_cell_length_a                   10.28200(10)
_cell_length_b                   15.9061(2)
_cell_length_c                   16.4165(2)
_cell_measurement_reflns_used    9860
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      66.42
_cell_measurement_theta_min      3.32
_cell_volume                     2477.10(5)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'ORTEP3 (Farraguia, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR92 (Giacavazzo, 1993)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 'ACTA 50'
_diffrn_measured_fraction_theta_max 0.934
_diffrn_measurement_device_type  'BRUKER APEX II CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0243
_diffrn_reflns_av_sigmaI/netI    0.0257
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            22680
_diffrn_reflns_theta_full        'ACTA 50'
_diffrn_reflns_theta_max         66.61
_diffrn_reflns_theta_min         2.90
_exptl_absorpt_coefficient_mu    4.082
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_correction_T_min  0.6872
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2008/1 (Bruker AXS)'
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.499
_exptl_crystal_description       square
_exptl_crystal_F_000             1148
_exptl_crystal_size_max          0.103
_exptl_crystal_size_mid          0.093
_exptl_crystal_size_min          0.057
_refine_diff_density_max         0.565
_refine_diff_density_min         -0.884
_refine_diff_density_rms         0.073
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     657
_refine_ls_number_reflns         8199
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.0467
_refine_ls_R_factor_gt           0.0438
_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^)+(0.0704P)^2^+3.4450P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1218
_refine_ls_wR_factor_ref         0.1246
_reflns_number_gt                7557
_reflns_number_total             8199
_reflns_threshold_expression     >2\s(I)
_cod_data_source_file            ja3079362_si_004.cif
_cod_data_source_block           kts3
_cod_database_code               4118772