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_4066969
_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            'C27 H33 F3 N2 O3 S'
_chemical_formula_weight         522.61
_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                90.106(2)
_cell_angle_beta                 106.203(2)
_cell_angle_gamma                103.980(2)
_cell_formula_units_Z            2
_cell_length_a                   9.6895(8)
_cell_length_b                   10.3646(8)
_cell_length_c                   13.2662(12)
_cell_measurement_reflns_used    7402
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.53
_cell_measurement_theta_min      2.26
_cell_volume                     1238.05(18)
_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 0.996
_diffrn_measured_fraction_theta_max 0.910
_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  0.0206
_diffrn_reflns_av_sigmaI/netI    0.0255
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            15496
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         28.71
_diffrn_reflns_theta_min         2.03
_exptl_absorpt_coefficient_mu    0.186
_exptl_absorpt_correction_T_max  0.9798
_exptl_absorpt_correction_T_min  0.8158
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.402
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             552
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.461
_refine_diff_density_min         -0.376
_refine_diff_density_rms         0.057
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    'NH free, rigid methyls, others riding'
_refine_ls_matrix_type           full
_refine_ls_number_parameters     337
_refine_ls_number_reflns         5821
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.0437
_refine_ls_R_factor_gt           0.0394
_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^)+(0.0526P)^2^+0.5948P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0982
_refine_ls_wR_factor_ref         0.1012
_reflns_number_gt                5275
_reflns_number_total             5821
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            om100738z_si_002.cif
_cod_data_source_block           jaf944bs
_cod_database_code               4066969