Rational and Predictable Chemoselective Synthesis of Oligoamines via Buchwald-Hartwig Amination of (Hetero)Aryl Chlorides Employing Mor-DalPhos
Bennett J. Tardiff; Robert McDonald; Michael J. Ferguson; Mark Stradiotto; Journal of Organic Chemistry 77 (2012) 1056–1071; doi:10.1021/jo202358p

data_4026908
_publ_section_title
;
 Rational and Predictable Chemoselective Synthesis of Oligoamines via
 Buchwald-Hartwig Amination of (Hetero)Aryl Chlorides Employing
 Mor-DalPhos
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              1056
_journal_page_last               1071
_journal_paper_doi               10.1021/jo202358p
_journal_volume                  77
_journal_year                    2012
_chemical_formula_moiety         'C45 H61 N3 O P Pd, C F3 O3 S, C H2 Cl2'
_chemical_formula_sum            'C47 H63 Cl2 F3 N3 O4 P Pd S'
_chemical_formula_weight         1031.33
_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                102.5936(7)
_cell_angle_beta                 96.5551(8)
_cell_angle_gamma                96.1075(7)
_cell_formula_units_Z            2
_cell_length_a                   10.6924(7)
_cell_length_b                   12.4945(8)
_cell_length_c                   18.4352(12)
_cell_measurement_reflns_used    9885
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.40
_cell_measurement_theta_min      2.25
_cell_volume                     2365.9(3)
_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-97 (Sheldrick, 2008)'
_computing_structure_solution    'DIRDIF-2008 (Beurskens et al., 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\w scans'
_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  0.0103
_diffrn_reflns_av_sigmaI/netI    0.0156
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            21291
_diffrn_reflns_theta_full        27.49
_diffrn_reflns_theta_max         27.49
_diffrn_reflns_theta_min         1.14
_exptl_absorpt_coefficient_mu    0.641
_exptl_absorpt_correction_T_max  0.8531
_exptl_absorpt_correction_T_min  0.7782
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2008)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.448
_exptl_crystal_description       prism
_exptl_crystal_F_000             1072
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.26
_refine_diff_density_max         0.876
_refine_diff_density_min         -1.307
_refine_diff_density_rms         0.074
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     645
_refine_ls_number_reflns         10798
_refine_ls_number_restraints     7
_refine_ls_restrained_S_all      1.066
_refine_ls_R_factor_all          0.0327
_refine_ls_R_factor_gt           0.0308
_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^)+(0.0466P)^2^+2.1454P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0843
_refine_ls_wR_factor_ref         0.0888
_reflns_number_gt                10218
_reflns_number_total             10798
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            jo202358p_si_001_1.cif
_cod_data_source_block           dal1092
_cod_database_code               4026908