C-H Bond Functionalization via Hydride Transfer: Formation of α-Arylated Piperidines and 1,2,3,4-Tetrahydroisoquinolines via Stereoselective Intramolecular Amination of Benzylic C-H Bonds
Paul A. Vadola; Ignacio Carrera; Dalibor Sames; Journal of Organic Chemistry 77 (2012) 6689–6702; doi:10.1021/jo300635m

data_4027374
_publ_section_title
;
 C-H Bond Functionalization via Hydride Transfer: Formation of \a-Arylated
 Piperidines and 1,2,3,4-Tetrahydroisoquinolines via Stereoselective
 Intramolecular Amination of Benzylic C-H Bonds
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              6689
_journal_page_last               6702
_journal_paper_doi               10.1021/jo300635m
_journal_volume                  77
_journal_year                    2012
_chemical_formula_sum            'C28 H25 N O2 S'
_chemical_formula_weight         439.55
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 92.9860(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   27.9292(15)
_cell_length_b                   8.1522(4)
_cell_length_c                   19.4546(10)
_cell_measurement_reflns_used    9931
_cell_measurement_temperature    125(2)
_cell_measurement_theta_max      32.60
_cell_measurement_theta_min      2.49
_cell_volume                     4423.5(4)
_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    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      125(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \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  0.0222
_diffrn_reflns_av_sigmaI/netI    0.0160
_diffrn_reflns_limit_h_max       39
_diffrn_reflns_limit_h_min       -39
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            34522
_diffrn_reflns_theta_full        30.50
_diffrn_reflns_theta_max         30.50
_diffrn_reflns_theta_min         1.46
_exptl_absorpt_coefficient_mu    0.173
_exptl_absorpt_correction_T_max  0.9829
_exptl_absorpt_correction_T_min  0.9295
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.320
_exptl_crystal_description       block
_exptl_crystal_F_000             1856
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.575
_refine_diff_density_min         -0.298
_refine_diff_density_rms         0.058
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     290
_refine_ls_number_reflns         6754
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0471
_refine_ls_R_factor_gt           0.0402
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0600P)^2^+3.5763P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1050
_refine_ls_wR_factor_ref         0.1118
_reflns_number_gt                5832
_reflns_number_total             6754
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo300635m_si_006.cif
_cod_data_source_block           pvas10
_cod_database_code               4027374