Palladium-Catalyzed Regio- and Enantioselective Fluorination of Acyclic Allylic Halides
Matthew H. Katcher; Allen Sha; Abigail G. Doyle; Journal of the American Chemical Society 133 (2011) 15902–15905; doi:10.1021/ja206960k

data_4106936
_publ_section_title
;
 Palladium-Catalyzed Regio- and Enantioselective Fluorination of Acyclic
 Allylic Halides
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              15902
_journal_page_last               15905
_journal_paper_doi               10.1021/ja206960k
_journal_volume                  133
_journal_year                    2011
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C16 H20 F N O2'
_chemical_formula_sum            'C16 H20 F N O2'
_chemical_formula_weight         277.33
_space_group_IT_number           1
_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                65.477(5)
_cell_angle_beta                 78.997(5)
_cell_angle_gamma                77.201(5)
_cell_formula_units_Z            2
_cell_length_a                   8.946(5)
_cell_length_b                   9.455(5)
_cell_length_c                   9.534(5)
_cell_measurement_reflns_used    6954
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      65.70
_cell_measurement_theta_min      5.10
_cell_volume                     711.0(7)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'ORTEP3 (Farraguia, 1993)'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR92 (Giacavazzo, 1994)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 'ACTA 50'
_diffrn_measured_fraction_theta_max 0.932
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0198
_diffrn_reflns_av_sigmaI/netI    0.0184
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            7932
_diffrn_reflns_theta_full        'ACTA 50'
_diffrn_reflns_theta_max         66.01
_diffrn_reflns_theta_min         5.10
_exptl_absorpt_coefficient_mu    0.768
_exptl_absorpt_correction_T_max  0.7527
_exptl_absorpt_correction_T_min  0.6890
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS v2008/1 (Bruker AXS)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.295
_exptl_crystal_description       shard
_exptl_crystal_F_000             296
_exptl_crystal_size_max          0.132
_exptl_crystal_size_mid          0.076
_exptl_crystal_size_min          0.033
_refine_diff_density_max         0.484
_refine_diff_density_min         -0.285
_refine_diff_density_rms         0.047
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 998'
_refine_ls_abs_structure_Flack   0.2(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.108
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     369
_refine_ls_number_reflns         2314
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.107
_refine_ls_R_factor_all          0.0400
_refine_ls_R_factor_gt           0.0392
_refine_ls_shift/su_max          0.038
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0680P)^2^+0.2575P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1061
_refine_ls_wR_factor_ref         0.1077
_reflns_number_gt                2271
_reflns_number_total             2314
_reflns_threshold_expression     >2\s(I)
_cod_data_source_file            ja206960k_si_001.cif
_cod_data_source_block           mhk1
_cod_database_code               4106936