Suzuki-Miyaura Cross-Coupling of Unprotected, Nitrogen-Rich Heterocycles: Substrate Scope and Mechanistic Investigation
M. Alexander Düfert; Kelvin L. Billingsley; Stephen L. Buchwald; Journal of the American Chemical Society 135 (2013) 12877–12885; doi:10.1021/ja4064469

data_4120389
_publ_section_title
;
 Suzuki-Miyaura Cross-Coupling of Unprotected, Nitrogen-Rich Heterocycles:
 Substrate Scope and Mechanistic Investigation
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              12877
_journal_page_last               12885
_journal_paper_doi               10.1021/ja4064469
_journal_volume                  135
_journal_year                    2013
_chemical_formula_sum            'C45.5 H59 N2 O3 P Pd'
_chemical_formula_weight         819.32
_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                109.424(2)
_cell_angle_beta                 93.059(3)
_cell_angle_gamma                116.144(2)
_cell_formula_units_Z            4
_cell_length_a                   16.574(2)
_cell_length_b                   16.933(2)
_cell_length_c                   17.319(2)
_cell_measurement_reflns_used    9811
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      31.56
_cell_measurement_theta_min      2.46
_cell_volume                     3998.6(8)
_computing_cell_refinement       'SAINT 7.46A (Bruker-AXS, 2011)'
_computing_data_collection       'APEX2 v2011.4.0 (Bruker-AXS, 2011)'
_computing_data_reduction        'SAINT 7.46A (Bruker-AXS, 2011)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 8.3
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker Smart APEX2 CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  'Incoatech ImuS multilayer optics'
_diffrn_radiation_source         'ImuS micro-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0489
_diffrn_reflns_av_sigmaI/netI    0.0389
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            159045
_diffrn_reflns_theta_full        31.35
_diffrn_reflns_theta_max         31.35
_diffrn_reflns_theta_min         1.28
_exptl_absorpt_coefficient_mu    0.547
_exptl_absorpt_correction_T_max  0.9891
_exptl_absorpt_correction_T_min  0.9323
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2009)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.361
_exptl_crystal_description       plate
_exptl_crystal_F_000             1724
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.02
_refine_diff_density_max         1.287
_refine_diff_density_min         -1.268
_refine_diff_density_rms         0.086
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1043
_refine_ls_number_reflns         26268
_refine_ls_number_restraints     443
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.0563
_refine_ls_R_factor_gt           0.0369
_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^)+(0.0308P)^2^+4.5193P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0809
_refine_ls_wR_factor_ref         0.0898
_reflns_number_gt                20410
_reflns_number_total             26268
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja4064469_si_002.cif
_cod_data_source_block           x12085
_cod_original_cell_volume        3998.4(9)
_cod_original_formula_sum        'C45.50 H59 N2 O3 P Pd'
_cod_database_code               4120389