From Olefination to Alkylation: In-Situ Halogenation of Julia-Kocienski Intermediates Leading to Formal Nucleophilic Iodo- and Bromodifluoromethylation of Carbonyl Compounds
Yanchuan Zhao; Bing Gao; Jinbo Hu; Journal of the American Chemical Society 134 (2012) 5790–5793; doi:10.1021/ja301601b

data_4117764
_publ_section_title
;
 From Olefination to Alkylation: In-Situ Halogenation of Julia-Kocienski
 Intermediates Leading to Formal Nucleophilic Iodo- and
 Bromodifluoromethylation of Carbonyl Compounds
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              5790
_journal_page_last               5793
_journal_paper_doi               10.1021/ja301601b
_journal_volume                  134
_journal_year                    2012
_chemical_formula_sum            'C17 H13 N O3 S'
_chemical_formula_weight         311.34
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_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                 91.641(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   15.9468(8)
_cell_length_b                   6.0282(4)
_cell_length_c                   15.2252(8)
_cell_measurement_reflns_used    3132
_cell_measurement_temperature    133(2)
_cell_measurement_theta_max      65.57
_cell_measurement_theta_min      5.81
_cell_volume                     1463.01(14)
_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      133(2)
_diffrn_measured_fraction_theta_full 0.975
_diffrn_measured_fraction_theta_max 0.975
_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  0.0662
_diffrn_reflns_av_sigmaI/netI    0.0513
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            13477
_diffrn_reflns_theta_full        65.00
_diffrn_reflns_theta_max         65.00
_diffrn_reflns_theta_min         5.81
_exptl_absorpt_coefficient_mu    2.076
_exptl_absorpt_correction_T_max  0.9795
_exptl_absorpt_correction_T_min  0.6249
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.414
_exptl_crystal_description       prism
_exptl_crystal_F_000             648
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.735
_refine_diff_density_min         -0.529
_refine_diff_density_rms         0.075
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         2414
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.1023
_refine_ls_R_factor_gt           0.0821
_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^)+(0.1122P)^2^+3.0074P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2135
_refine_ls_wR_factor_ref         0.2361
_reflns_number_gt                1835
_reflns_number_total             2414
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja301601b_si_004.cif
_cod_data_source_block           cu_dm11521_0ma
_cod_database_code               4117764