Eight-Membered Palladacycles Derived from the Insertion of Olefins into the Pd−C Bond of Ortho-Palladated Pharmaceuticals Phenethylamine and Phentermine. Synthesis of Stable Heck-Type Intermediates Containing Accessible β-Hydrogens and Its Use in the Synthesis of 2-Styrylphenethylamines, Tetrahydroisoquinolines, and Eight-Membered Cyclic Amidines†
Vicente, José; Saura-Llamas, Isabel; García-López, José-Antonio; Bautista, Delia; Organometallics 29 (2010) 4320–; doi:10.1021/om100738z

data_4066968
_publ_section_title
;
 Eight-Membered Palladacycles Derived from the Insertion of Olefins into
 the Pd&#x2212;C Bond of Ortho-Palladated Pharmaceuticals Phenethylamine
 and Phentermine. Synthesis of Stable Heck-Type Intermediates Containing
 Accessible \b-Hydrogens and Its Use in the Synthesis of
 2-Styrylphenethylamines, Tetrahydroisoquinolines, and Eight-Membered
 Cyclic Amidines&#x2020;
;
_journal_issue                   19
_journal_name_full               Organometallics
_journal_page_first              4320
_journal_paper_doi               10.1021/om100738z
_journal_volume                  29
_journal_year                    2010
_chemical_formula_sum            'C28 H29 Cl N P Pd'
_chemical_formula_weight         552.34
_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                98.737(2)
_cell_angle_beta                 108.481(2)
_cell_angle_gamma                113.649(2)
_cell_formula_units_Z            2
_cell_length_a                   9.9381(3)
_cell_length_b                   11.6534(4)
_cell_length_c                   12.6531(4)
_cell_measurement_reflns_used    9962
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.12
_cell_measurement_theta_min      2.22
_cell_volume                     1205.64(8)
_computing_cell_refinement       'BRUKER SAINT'
_computing_data_collection       'BRUKER SMART'
_computing_data_reduction        'BRUKER SAINT'
_computing_molecular_graphics    'BRUKER SHELXTL'
_computing_publication_material  'BRUKER SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 8.26
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.914
_diffrn_measurement_device_type  'Bruker SMART APEX CCD'
_diffrn_measurement_method       \w-scan
_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  0.0168
_diffrn_reflns_av_sigmaI/netI    0.0216
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            13985
_diffrn_reflns_theta_full        26.50
_diffrn_reflns_theta_max         28.12
_diffrn_reflns_theta_min         2.01
_exptl_absorpt_coefficient_mu    0.963
_exptl_absorpt_correction_T_max  0.9445
_exptl_absorpt_correction_T_min  0.8160
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.521
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             564
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.425
_refine_diff_density_min         -0.288
_refine_diff_density_rms         0.071
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_hydrogen_treatment    'NH2 free, rigid methyls others riding'
_refine_ls_matrix_type           full
_refine_ls_number_parameters     299
_refine_ls_number_reflns         5394
_refine_ls_number_restraints     25
_refine_ls_restrained_S_all      1.069
_refine_ls_R_factor_all          0.0246
_refine_ls_R_factor_gt           0.0237
_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^)+(0.0242P)^2^+1.1334P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0572
_refine_ls_wR_factor_ref         0.0577
_reflns_number_gt                5222
_reflns_number_total             5394
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            om100738z_si_002.cif
_cod_data_source_block           jad762s
_cod_original_cell_volume        1205.64(7)
_cod_database_code               4066968