Fluoroalkylative aryl migration of conjugated N-arylsulfonylated amides using easily accessible sodium di- and monofluoroalkanesulfinates.
He, Zhengbiao; Tan, Ping; Ni, Chuanfa; Hu, Jinbo; Organic letters 17 (2015) 1838–1841; doi:10.1021/acs.orglett.5b00308

data_1554815
_publ_section_title
;
 Fluoroalkylative aryl migration of conjugated N-arylsulfonylated amides
 using easily accessible sodium di- and monofluoroalkanesulfinates.
;
_journal_issue                   8
_journal_name_full               'Organic letters'
_journal_page_first              1838
_journal_page_last               1841
_journal_paper_doi               10.1021/acs.orglett.5b00308
_journal_volume                  17
_journal_year                    2015
_chemical_formula_moiety         'C19 H21 F2 N O'
_chemical_formula_sum            'C19 H21 F2 N O'
_chemical_formula_weight         317.37
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/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                 90.259(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.9286(7)
_cell_length_b                   17.0093(13)
_cell_length_c                   10.0841(8)
_cell_measurement_reflns_used    4211
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      66.87
_cell_measurement_theta_min      2.60
_cell_volume                     1703.0(2)
_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      296(2)
_diffrn_measured_fraction_theta_full 0.887
_diffrn_measured_fraction_theta_max 0.887
_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           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0289
_diffrn_reflns_av_sigmaI/netI    0.0333
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            7100
_diffrn_reflns_theta_full        65.96
_diffrn_reflns_theta_max         65.96
_diffrn_reflns_theta_min         4.45
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.750
_exptl_absorpt_correction_T_max  0.7529
_exptl_absorpt_correction_T_min  0.5416
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.238
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       flaky
_exptl_crystal_F_000             672
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.233
_refine_diff_density_min         -0.156
_refine_diff_density_rms         0.037
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         2628
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.015
_refine_ls_R_factor_all          0.0581
_refine_ls_R_factor_gt           0.0534
_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^)+(0.0939P)^2^+0.4763P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1608
_refine_ls_wR_factor_ref         0.1673
_reflns_number_gt                2302
_reflns_number_total             2628
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol5b00308_si_002.cif
_cod_data_source_block           233
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               1554815